(2R,3R,4R)-2-(hydroxymethyl)-3,4-dihydro-2H-pyran-3,4-diol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Galactal 7′ (0.100 g, 0.304 mmol) in 5 mL dry CH2Cl2 at 0° C. under a N2 atmosphere was treated with 10 mL Murray solution (freshly prepared) and stirred at 0° C. for 40 min. TLC (1:1 EtOAc:hex) showed no trace of 7′. Solvents were evaporated using a dry N2 stream. The residual epoxide of 7′ was kept on a vac. line ˜2 h. To the epoxide under a N2 atmosphere was added a solution of glucal derivative 3′ (0.150 g, 0.496 mmol) in 3 mL dry THF. On cooling to −78° C., 1.0 M ZnCl2 in Et2O (0.50 mL, 0.50 mmol) was added. The mixture was allowed to slowly warm to r.t. (over ˜2 h) and stirred overnight. TLC (1:1 EtOAc:hex) showed that the reaction was complete. Saturated aq. NaHCO3 (20 mL) was added, and the mixture was then extracted with EtOAc (3×20 mL). The organic layer was dried over MgSO4. Column chromatography on silica (1:3 EtOAc:hex) afforded diol 18′ as a colorless solid. Yield: 173 mg (89%). [α]D23 −9.8° (c 1.0, CH2Cl2). freshly prepared) and Solvents were evaporated line ˜2 h To the epoxide under a N2 atmosphere was added a solution of glucal derivative 3′ (0.150 g, 0.496 mmol) in 3 mL dry THF On cooling to −78° C. to slowly warm to r.t. (over ˜2 h) stirred overnight the mixture was then extracted with EtOAc (3×20 mL) The organic layer was dried over MgSO4

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Galactal 7' (0.100 g, 0.304 mmol) in 5 mL dry CH2Cl2 at 0° C. under a N2 atmosphere was treated with 10 mL Murray solution (freshly prepared) and stirred at 0° C. for 40 min. TLC (1:1 EtOAc:hex) showed no trace of 7'. Solvents were evaporated using a dry N2 stream. The residual epoxide of 7' was kept on a vac. line ~2h. To the epoxide under a N2 atmosphere was added a solution of glucal derivative 3' (0.150 g, 0.496 mmol) in 3 mL dry THF. On cooling to -78° C., 1.0M ZnCl2 in Et2O (0.50 mL, 0.50 mmol) was added. The mixture was allowed to slowly warm to r.t. (over ~2 h) and stirred overnight. TLC (1:1 EtOAc:hex) showed that the reaction was complete. Saturated aq. NaHCO3 (20 mL) was added, and the mixture was then extracted with EtOAc (3×20 mL). The organic layer was dried over MgSO4. Column chromatography on silica (1:3 EtOAc:hex) afforded diol 18' as a colorless solid. Yield: 173 mg (89%). [α]D23 -9.8° (c 1.0, CH2Cl2). freshly prepared) and Solvents were evaporated line ~2h To the epoxide under a N2 atmosphere was added a solution of glucal derivative 3' (0.150 g, 0.496 mmol) in 3 mL dry THF On cooling to -78° C. to slowly warm to r.t. (over ~2 h) stirred overnight the mixture was then extracted with EtOAc (3×20 mL) The organic layer was dried over MgSO4

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Galactal 7' (0.100 g, 0.304 mmol) in 5 mL dry CH2Cl2 at 0° C. under a N2 atmosphere was treated with 10 mL Murray solution (freshly prepared) and stirred at 0° C. for 40 min. TLC (1:1 EtOAc:hex) showed no trace of 7'. Solvents were evaporated using a dry N2 stream. The residual epoxide of 7' was kept on a vac. line ~2h. To the epoxide under a N2 atmosphere was added a solution of glucal derivative 3' (0.150 g, 0.496 mmol) in 3 mL dry THF. On cooling to -78° C., 1.0M ZnCl2 in Et2O (0.50 mL, 0.50 mmol) was added. The mixture was allowed to slowly warm to r.t. (over ~2 h) and stirred overnight. TLC (1:1 EtOAc:hex) showed that the reaction was complete. Saturated aq. NaHCO3 (20 mL) was added, and the mixture was then extracted with EtOAc (3×20 mL). The organic layer was dried over MgSO4. Column chromatography on silica (1:3 EtOAc:hex) afforded diol 18' as a colorless solid. Yield: 173 mg (89%). [α]D23 -9.8° (c 1.0, CH2Cl2). freshly prepared) and Solvents were evaporated line ~2h To the epoxide under a N2 atmosphere was added a solution of glucal derivative 3' (0.150 g, 0.496 mmol) in 3 mL dry THF On cooling to -78° C. to slowly warm to r.t. (over ~2 h) stirred overnight the mixture was then extracted with EtOAc (3×20 mL) The organic layer was dried over MgSO4

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Galactal 7' (0.100 g, 0.304 mmol) in 5 mL dry CH2Cl2 at 0° C. under a N2 atmosphere was treated with 10 mL Murray solution (freshly prepared) and stirred at 0° C. for 40 min. TLC (1:1 EtOAc:hex) showed no trace of 7'. Solvents were evaporated using a dry N2 stream. The residual epoxide of 7' was kept on a vac. line ~2 h. To the epoxide under a N2 atmosphere was added a solution of glucal derivative 3' (0.150 g, 0.496 mmol) in 3 mL dry THF. On cooling to -78° C., 1.0M ZnCl2 in Et2O (0.50 mL, 0.50 mmol) was added. The mixture was allowed to slowly warm to r.t. (over ~2 h) and stirred overnight. TLC (1:1 EtOAc:hex) showed that the reaction was complete. Saturated aq. NaHCO3 (20 mL) was added, and the mixture was then extracted with EtOAc (3×20 mL). The organic layer was dried over MgSO4. Column chromatography on silica (1:3 EtOAc:hex) afforded diol 18' as a colorless solid. Yield: 173 mg (89%). [α]D23 -9.8° (c 1.0, CH2Cl2). freshly prepared) and Solvents were evaporated line ~2 h To the epoxide under a N2 atmosphere was added a solution of glucal derivative 3' (0.150 g, 0.496 mmol) in 3 mL dry THF On cooling to -78° C. to slowly warm to r.t. (over ~2 h) stirred overnight the mixture was then extracted with EtOAc (3×20 mL) The organic layer was dried over MgSO4

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Galactal 7' (0.100 g, 0.304 mmol) in 5 mL dry CH2Cl2 at 0° C. under a N2 atmosphere was treated with 10 mL Murray solution (freshly prepared) and stirred at 0° C. for 40 min. TLC (1:1 EtOAc:hex) showed no trace of 7'. Solvents were evaporated using a dry N2 stream. The residual epoxide of 7' was kept on a vac. line ~2 h. To the epoxide under a N2 atmosphere was added a solution of glucal derivative 3' (0.150 g, 0.496 mmol) in 3 mL dry THF. On cooling to -78° C., 1.0M ZnCl2 in Et2O (0.50 mL, 0.50 mmol) was added. The mixture was allowed to slowly warm to r.t. (over ~2 h) and stirred overnight. TLC (1:1 EtOAc:hex) showed that the reaction was complete. Saturated aq. NaHCO3 (20 mL) was added, and the mixture was then extracted with EtOAc (3×20 mL). The organic layer was dried over MgSO4. Column chromatography on silica (1:3 EtOAc:hex) afforded diol 18' as a colorless solid. Yield: 173 mg (89%). [α]D23 -9.8° (c 1.0, CH2Cl2). freshly prepared) and Solvents were evaporated line ~2 h To the epoxide under a N2 atmosphere was added a solution of glucal derivative 3' (0.150 g, 0.496 mmol) in 3 mL dry THF On cooling to -78° C. to slowly warm to r.t. (over ~2 h) stirred overnight the mixture was then extracted with EtOAc (3×20 mL) The organic layer was dried over MgSO4

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2.00 g (2.47 mmol) of lactal carbonate 8c was added 4.44 g (9.86 mmol) of fucosyl fluoride 9c. The mixture was azeotroped 5 times with benzene and placed under high vacuum for two hours. Under an argon atmosphere 2.77 mL (12.33 mmol) of di-tert-butyl pyridine and 16 mL of dry ether were added. 2.0 g of freshly activated 4 Å molecular sieves were added and the mixture stirred one hour at room temperature. In an argon glove bag, 2.34 g (12.33 mmol) of stannous chloride (SnCl2) and 2.56 g (12.33 mmol) of silver perchlorate (AgClO4) were added. The flask was equipped with a reflux condenser and the reaction brought to reflux for 72 hours. The reaction was quenched with 5 mL of saturated bicarbonate and filtered through a pad of celite. Diluted with 50 mL ethyl acetate and washed 2 times with saturated bicarbonate, 2 times with sat. copper sulfate and 2 times with sat. brine. The organics were dried over MgSO4 and concentrated. Flash chromatography in 20% ethyl acetate/hexanes afforded 2.10 g (51%) of a white foam 10 c: The mixture was azeotroped 5 times with benzene 2.0 g of freshly activated 4 Å molecular sieves were added The flask was equipped with a reflux condenser to reflux for 72 hours The reaction was quenched with 5 mL of saturated bicarbonate filtered through a pad of celite Diluted with 50 mL ethyl acetate washed 2 times with saturated bicarbonate, 2 times with sat. copper sulfate and 2 times with sat. brine The organics were dried over MgSO4 concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2.00 g (2.47 mmol) of lactal carbonate 8c was added 4.44 g (9.86 mmol) of fucosyl fluoride 9c. The mixture was azeotroped 5 times with benzene and placed under high vacuum for two hours. Under an argon atmosphere 2.77 mL (12.33 mmol) of di-tert-butyl pyridine and 16 mL of dry ether were added. 2.0 g of freshly activated 4 Å molecular sieves were added and the mixture stirred one hour at room temperature. In an argon glove bag, 2.34 g (12.33 mmol) of stannous chloride (SnCl2) and 2.56 g (12.33 mmol) of silver perchlorate (AgClO4) were added. The flask was equipped with a reflux condenser and the reaction brought to reflux for 72 hours. The reaction was quenched with 5 mL of saturated bicarbonate and filtered through a pad of celite. Diluted with 50 mL ethyl acetate and washed 2 times with saturated bicarbonate, 2 times with sat. copper sulfate and 2 times with sat. brine. The organics were dried over MgSO4 and concentrated. Flash chromatography in 20% ethyl acetate/hexanes afforded 2.10 g (51%) of a white foam 10 c: The mixture was azeotroped 5 times with benzene 2.0 g of freshly activated 4 Å molecular sieves were added The flask was equipped with a reflux condenser to reflux for 72 hours The reaction was quenched with 5 mL of saturated bicarbonate filtered through a pad of celite Diluted with 50 mL ethyl acetate washed 2 times with saturated bicarbonate, 2 times with sat. copper sulfate and 2 times with sat. brine The organics were dried over MgSO4 concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Galactal 7′ (0.100 g, 0.304 mmol) in 5 mL dry CH2Cl2 at 0° C. under a N2 atmosphere was treated with 10 mL Murray solution (freshly prepared) and stirred at 0° C. for 40 min. TLC (1:1 EtOAc:hex) showed no trace of 7′. Solvents were evaporated using a dry N2 stream. The residual epoxide of 7′ was kept on a vac. line ˜2 h. To the epoxide under a N2 atmosphere was added a solution of glucal derivative 3′ (0.150 g, 0.496 mmol) in 3 mL dry THF. On cooling to −78° C., 1.0 M ZnCl2 in Et2O (0.50 mL, 0.50 mmol) was added. The mixture was allowed to slowly warm to r.t. (over ˜2 h) and stirred overnight. TLC (1:1 EtOAc:hex) showed that the reaction was complete. Saturated aq. NaHCO3 (20 mL) was added, and the mixture was then extracted with EtOAc (3×20 mL). The organic layer was dried over MgSO4. Column chromatography on silica (1:3 EtOAc:hex) afforded diol 18′ as a colorless solid. Yield: 173 mg (89%). [α]D23−9.8° (c 1.0, CH2Cl2). freshly prepared) and Solvents were evaporated line ˜2 h To the epoxide under a N2 atmosphere was added a solution of glucal derivative 3′ (0.150 g, 0.496 mmol) in 3 mL dry THF On cooling to −78° C. to slowly warm to r.t. (over ˜2 h) stirred overnight the mixture was then extracted with EtOAc (3×20 mL) The organic layer was dried over MgSO4

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Galactal 7′ (0.100 g, 0.304 mmol) in 5 mL dry CH2Cl2 at 0° C. under a N2 atmosphere was treated with 10 mL Murray solution (freshly prepared) and stirred at 0° C. for 40 min. TLC (1:1 EtOAc:hex) showed no trace of 7′. Solvents were evaporated using a dry N2 stream. The residual epoxide of 7′ was kept on a vac. line ˜2 h. To the epoxide under a N2 atmosphere was added a solution of glucal derivative 3′ (0.150 g, 0.496 mmol) in 3 mL dry THF. On cooling to −78° C., 1.0 M ZnCl2 in Et2O (0.50 mL, 0.50 mmol) was added. The mixture was allowed to slowly warm to r.t. (over ˜2 h) and stirred overnight. TLC (1:1 EtOAc:hex) showed that the reaction was complete. Saturated aq. NaHCO3 (20 mL) was added, and the mixture was then extracted with EtOAc (3×20 mL). The organic layer was dried over MgSO4. Column chromatography on silica (1:3 EtOAc:hex) afforded diol 18′ as a colorless solid. Yield: 173 mg (89%). [α]D23 −9.8° (c 1.0, CH2Cl2). freshly prepared) and Solvents were evaporated line ˜2 h To the epoxide under a N2 atmosphere was added a solution of glucal derivative 3′ (0.150 g, 0.496 mmol) in 3 mL dry THF On cooling to −78° C. to slowly warm to r.t. (over ˜2 h) stirred overnight the mixture was then extracted with EtOAc (3×20 mL) The organic layer was dried over MgSO4

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Galactal 7' (0.100 g, 0.304 mmol) in 5 mL dry CH2Cl2 at 0° C. under a N2 atmosphere was treated with 10 mL Murray solution (freshly prepared) and stirred at 0° C. for 40 min. TLC (1:1 EtOAc:hex) showed no trace of 7'. Solvents were evaporated using a dry N2 stream. The residual epoxide of 7' was kept on a vac. line ~2 h. To the epoxide under a N2 atmosphere was added a solution of glucal derivative 3' (0.150 g, 0.496 mmol) in 3 mL dry THF. On cooling to -78° C., 1.0 M ZnCl2 in Et2O (0.50 mL, 0.50 mmol) was added. The mixture was allowed to slowly warm to r.t. (over ~2 h) and stirred overnight. TLC (1:1 EtOAc:hex) showed that the reaction was complete. Saturated aq. NaHCO3 (20 mL) was added, and the mixture was then extracted with EtOAc (3×20 mL). The organic layer was dried over MgSO4. Column chromatography on silica (1:3 EtOAc:hex) afforded diol 18' as a colorless solid. Yield: 173 mg (89%). [α]D23 -9.8° (c 1.0, CH2Cl2). freshly prepared) and Solvents were evaporated line ~2 h To the epoxide under a N2 atmosphere was added a solution of glucal derivative 3' (0.150 g, 0.496 mmol) in 3 mL dry THF On cooling to -78° C. to slowly warm to r.t. (over ~2 h) stirred overnight the mixture was then extracted with EtOAc (3×20 mL) The organic layer was dried over MgSO4

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Galactal 7' (0.100 g, 0.304 mmol) in 5 mL dry CH2Cl2 at 0° C. under a N2 atmosphere was treated with 10 mL Murray solution (freshly prepared) and stirred at 0° C. for 40 min. TLC (1:1 EtOAc:hex) showed no trace of 7'. Solvents were evaporated using a dry N2 stream. The residual epoxide of 7' was kept on a vac. line ~2 h. To the epoxide under a N2 atmosphere was added a solution of glucal derivative 3' (0.150 g, 0.496 mmol) in 3 mL dry THF. On cooling to -78° C., 1.0 M ZnCl2 in Et2O (0.50 mL, 0.50 mmol) was added. The mixture was allowed to slowly warm to r.t. (over ~2 h) and stirred overnight. TLC (1:1 EtOAc:hex) showed that the reaction was complete. Saturated aq. NaHCO3 (20 mL) was added, and the mixture was then extracted with EtOAc (3×20 mL). The organic layer was dried over MgSO4. Column chromatography on silica (1:3 EtOAc:hex) afforded diol 18' as a colorless solid. Yield: 173 mg (89%). [α]D23 -9.8° (c 1.0, CH2Cl2). freshly prepared) and Solvents were evaporated line ~2 h To the epoxide under a N2 atmosphere was added a solution of glucal derivative 3' (0.150 g, 0.496 mmol) in 3 mL dry THF On cooling to -78° C. to slowly warm to r.t. (over ~2 h) stirred overnight the mixture was then extracted with EtOAc (3×20 mL) The organic layer was dried over MgSO4

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Galactal 7' (0.100 g, 0.304 mmol) in 5 mL dry CH2Cl2 at 0° C. under a N2 atmosphere was treated with 10 mL Murray solution (freshly prepared) and stirred at 0° C. for 40 min. TLC (1:1 EtOAc:hex) showed no trace of 7'. Solvents were evaporated using a dry N2 stream. The residual epoxide of 7' was kept on a vac. line ~2 h. To the epoxide under a N2 atmosphere was added a solution of glucal derivative 3' (0.150 g, 0.496 mmol) in 3 mL dry THF. On cooling to -78° C., 1.0 M ZnCl2 in Et2O (0.50 mL, 0.50 mmol) was added. The mixture was allowed to slowly warm to r.t. (over ~2 h) and stirred overnight. TLC (1:1 EtOAc:hex) showed that the reaction was complete. Saturated aq. NaHCO3 (20 mL) was added, and the mixture was then extracted with EtOAc (3×20 mL). The organic layer was dried over MgSO4. Column chromatography on silica (1:3 EtOAc:hex) afforded diol 18' as a colorless solid. Yield: 173 mg (89%). [α]D23 -9.8° (c 1.0, CH2Cl2). freshly prepared) and Solvents were evaporated line ~2 h To the epoxide under a N2 atmosphere was added a solution of glucal derivative 3' (0.150 g, 0.496 mmol) in 3 mL dry THF On cooling to -78° C. to slowly warm to r.t. (over ~2 h) stirred overnight the mixture was then extracted with EtOAc (3×20 mL) The organic layer was dried over MgSO4