Реакция #83093

Уравнение реакции

product

1-Amino-2,5-anhydro-1,3-dideoxy-6-O-[(1,1-dimethylethyl)diphenylsilyl]-D-arabino-hexitol

potassium carbonate

p-nitrobenzyl chloroformate

→

desired product

Выход 75.6%

2,5-Anhydro-1,3-dideoxy-6-O-[(1,1-dimethylethyl)diphenylsilyl]-1-[[[(4-nitrophenyl)methoxy]carbonyl]amino]-D-arabino-hexitol

Выход 75.6%

Растворители

tetrahydrofuran

water

Условия реакции

Обработка

1. 1
   Экстракцияextracted with 3×100 ml of ethyl acetate
2. 2
   Другоеdried
3. 3
   Концентрированиеconcentrated in vacuo
4. 4
   Другоеpurified by chromatography (Silica Gel: 5-50% ethyl acetate/hexane)

Методика

A slurry of 3.15 g of product from Example 283 and 1.35 g of potassium carbonate in 15 ml of tetrahydrofuran at 0° C., under argon, is treated with 2.11 g of p-nitrobenzyl chloroformate and the reaction is stirred vigorously at 0° C. for 4 hours. The reaction mixture is diluted with 100 ml of water, extracted with 3×100 ml of ethyl acetate, dried, concentrated in vacuo and purified by chromatography (Silica Gel: 5-50% ethyl acetate/hexane) to give 3.49 g of the desired product.

Источник