(2S,3S,4R,5S)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol

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

Procedure: The trifluoroacetate obtained by the same operation as in EXAMPLE 26 by using 800 mg (0.86 mmol) of benzhydryl 3-iodomethyl-7β-[2-ethoxyimino-2-(2-tritylaminothiazol-4-yl) acetamido]-3-cephem-4-carboxylate (syn-isomer) and 300 mg (1.33 mmol) of 2-mercapto-5-(3,4-dihydroxyphenyl)-1,3, 4-thiadiazole, was suspended in water and adjusted to pH6.5 with a saturated sodium hydrogencarbonate. The suspension was subjected to ODS column chromatography (LC Sorb RP-18, manufactured by Kemco Co.) and eluted with a 40% methanol aqueous solution. The fraction containing the desired compound was concentrated and freeze-dried to obtain 106 mg (yield: 16.6%) of the above identified compound. eluted with a 40% methanol aqueous solution The fraction containing the desired compound was concentrated freeze-dried to obtain 106 mg (yield: 16.6%) of the

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

Procedure: A trifluoroacetate obtained by the same operation as in EXAMPLE 1 by using 1.0 g (1.07 mmol) of benzhydryl 3-iodomethyl-7β-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl) acetamido]-3-cephem-4-carboxylate (syn-isomer) and 0.43 g (1.07 mmol) of 2-mercapto-5-[3,4-di(2-methoxyethoxymethoxy)phenyl]-1,3,4-thiadiazole, was suspended in water and adjusted to pH6.5 with a saturated sodium hydrogencarbonate aqueous solution. Then, the suspension was subjected to ODS column chromatography (LC Sorb RP-18, manufactured by Kemco Co.) and eluted with a 20% methanol aqueous solution. The fraction containing the desired compound was concentrated and freeze-dried to obtain 168 mg (yield: 24.3%) of the above identified compound. eluted with a 20% methanol aqueous solution The fraction containing the desired compound was concentrated freeze-dried to obtain 168 mg (yield: 24.3%) of the

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

Procedure: The trifluoroacetate obtained by the same operation as in EXAMPLE 26 by using 800 mg (0.86 mmol) of benzhydryl 3-iodomethyl-7β-[2-ethoxyimino-2-(2-tritylaminothiazol-4-yl) acetamido]-3-cephem-4-carboxylate (syn-isomer) and 300 mg (1.33 mmol) of 2-mercapto-5-(3,4-dihydroxyphenyl)-1,3, 4-thiadiazole, was suspended in water and adjusted to pH6.5 with a saturated sodium hydrogencarbonate. The suspension was subjected to ODS column chromatography (LC Sorb RP-18, manufactured by Kemco Co.) and eluted with a 40% methanol aqueous solution. The fraction containing the desired compound was concentrated and freeze-dried to obtain 106 mg (yield: 16.6%) of the above identified compound. eluted with a 40% methanol aqueous solution The fraction containing the desired compound was concentrated freeze-dried to obtain 106 mg (yield: 16.6%) of the

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

Procedure: The trifluoroacetate obtained by the same operation as in EXAMPLE 26 by using 800 mg (0.86 mmol) of benzhydryl 3-iodomethyl-7β-[2-ethoxyimino-2-(2-tritylaminothiazol-4-yl) acetamido]-3-cephem-4-carboxylate (syn-isomer) and 300 mg (1.33 mmol) of 2-mercapto-5-(3,4-dihydroxyphenyl)-1,3, 4-thiadiazole, was suspended in water and adjusted to pH6.5 with a saturated sodium hydrogencarbonate. The suspension was subjected to ODS column chromatography (LC Sorb RP-18, manufactured by Kemco Co.) and eluted with a 40% methanol aqueous solution. The fraction containing the desired compound was concentrated and freeze-dried to obtain 106 mg (yield: 16.6%) of the above identified compound. eluted with a 40% methanol aqueous solution The fraction containing the desired compound was concentrated freeze-dried to obtain 106 mg (yield: 16.6%) of the

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

Procedure: A trifluoroacetate obtained by the same operation as in EXAMPLE 1 by using 1.0 g (1.07 mmol) of benzhydryl 3-iodomethyl-7β-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl) acetamido]-3-cephem-4-carboxylate (syn-isomer) and 0.43 g (1.07 mmol) of 2-mercapto-5-[3,4-di(2-methoxyethoxymethoxy)phenyl]-1,3,4-thiadiazole, was suspended in water and adjusted to pH6.5 with a saturated sodium hydrogencarbonate aqueous solution. Then, the suspension was subjected to ODS column chromatography (LC Sorb RP-18, manufactured by Kemco Co.) and eluted with a 20% methanol aqueous solution. The fraction containing the desired compound was concentrated and freeze-dried to obtain 168 mg (yield: 24.3%) of the above identified compound. eluted with a 20% methanol aqueous solution The fraction containing the desired compound was concentrated freeze-dried to obtain 168 mg (yield: 24.3%) of the

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

Procedure: A trifluoroacetate obtained by the same operation as in EXAMPLE 1 by using 1.0 g (1.07 mmol) of benzhydryl 3-iodomethyl-7β-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl) acetamido]-3-cephem-4-carboxylate (syn-isomer) and 0.43 g (1.07 mmol) of 2-mercapto-5-[3,4-di(2-methoxyethoxymethoxy)phenyl]-1,3,4-thiadiazole, was suspended in water and adjusted to pH6.5 with a saturated sodium hydrogencarbonate aqueous solution. Then, the suspension was subjected to ODS column chromatography (LC Sorb RP-18, manufactured by Kemco Co.) and eluted with a 20% methanol aqueous solution. The fraction containing the desired compound was concentrated and freeze-dried to obtain 168 mg (yield: 24.3%) of the above identified compound. eluted with a 20% methanol aqueous solution The fraction containing the desired compound was concentrated freeze-dried to obtain 168 mg (yield: 24.3%) of the

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

Procedure: The trifluoroacetate obtained by the same operation as in EXAMPLE 26 by using 800 mg (0.86 mmol) of benzhydryl 3-iodomethyl-7β-[2-ethoxyimino-2-(2-tritylaminothiazol-4-yl) acetamido]-3-cephem-4-carboxylate (syn-isomer) and 300 mg (1.33 mmol) of 2-mercapto-5-(3,4-dihydroxyphenyl)-1,3, 4-thiadiazole, was suspended in water and adjusted to pH6.5 with a saturated sodium hydrogencarbonate. The suspension was subjected to ODS column chromatography (LC Sorb RP-18, manufactured by Kemco Co.) and eluted with a 40% methanol aqueous solution. The fraction containing the desired compound was concentrated and freeze-dried to obtain 106 mg (yield: 16.6%) of the above identified compound. eluted with a 40% methanol aqueous solution The fraction containing the desired compound was concentrated freeze-dried to obtain 106 mg (yield: 16.6%) of the

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

Procedure: A trifluoroacetate obtained by the same operation as in EXAMPLE 1 by using 1.0 g (1.07 mmol) of benzhydryl 3-iodomethyl-7β-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl) acetamido]-3-cephem-4-carboxylate (syn-isomer) and 0.43 g (1.07 mmol) of 2-mercapto-5-[3,4-di(2-methoxyethoxymethoxy)phenyl]-1,3,4-thiadiazole, was suspended in water and adjusted to pH6.5 with a saturated sodium hydrogencarbonate aqueous solution. Then, the suspension was subjected to ODS column chromatography (LC Sorb RP-18, manufactured by Kemco Co.) and eluted with a 20% methanol aqueous solution. The fraction containing the desired compound was concentrated and freeze-dried to obtain 168 mg (yield: 24.3%) of the above identified compound. eluted with a 20% methanol aqueous solution The fraction containing the desired compound was concentrated freeze-dried to obtain 168 mg (yield: 24.3%) of the