2-[2-[2-[2-(2-trityloxyethoxy)ethoxy]ethoxy]ethoxy]ethanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of Compound 2 (4.3 g, 8.9 mmol) in toluene (20 ml), tributylphosphine (2.35 g, 8.92 mmol) was added at room temperature; this was followed by stirring for 1 hour. This was gradually added to a solution of Compound 43 (3.3 g, 11.6 mmol) and 1,1′-azobis(N,N-dimethylformamide) (2.0 g, 11.6 mmol) in toluene (20 ml), and this was followed by overnight stirring at room temperature. Ethyl acetate (100 ml) was added; the resulting insoluble matter was removed by Celite filtration and washed with ethyl acetate. The combined organic phases were concentrated under reduced pressure; the residue obtained was purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (n-hexane:ethyl acetate 3:1-2:1)) to yield Compound 44 (colorless oil 2.8 g, 39%). this was followed by overnight stirring at room temperature the resulting insoluble matter was removed by Celite filtration washed with ethyl acetate The combined organic phases were concentrated under reduced pressure the residue obtained was purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (n-hexane:ethyl acetate 3:1-2:1))

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

Procedure: To a solution of Compound 2 (2.8 g, 5.8 mmol) in toluene (10 ml), a solution of tributylphosphine (1.17 g, 5.8 mmol) in toluene (2 ml) was added at room temperature; this was followed by stirring for 1 hour. This was gradually added to a solution of Compound 18 (1.1 g, 4.9 mmol) and 1,1′-azobis(N,N-dimethylformamide) (1.0 g, 5.8 mmol) in toluene (10 ml), and this was followed by overnight stirring at room temperature. Ethyl acetate was added; the resulting insoluble matter was removed by Celite filtration, and washing was conducted with ethyl acetate. The combined organic phases were concentrated under reduced pressure; the residue obtained was purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (n-hexane:ethyl acetate 2:1)) to yield Compound 21 (colorless oil 2.03 g, 60%). this was followed by overnight stirring at room temperature the resulting insoluble matter was removed by Celite filtration washing The combined organic phases were concentrated under reduced pressure the residue obtained was purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (n-hexane:ethyl acetate 2:1))

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

Procedure: 10 g of pentaethyleneglycol was dissolved in a mixture of 100 mL of acetonitrile and 30 mL of pyridine, to which 11 g of trityl chloride were added at 0° C., and then the solution was stirred overnight at room temperature. The reaction solution was mixed with iced water and subjected to extraction with ethyl acetate, and then the organic layer washed with water and concentrated under reduced pressure after drying. The residue was purified with silica gel column chromatography to obtain 6 g of the objective compound. were added at 0° C. subjected to extraction with ethyl acetate the organic layer washed with water concentrated under reduced pressure after drying The residue was purified with silica gel column chromatography