Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 54815Generated: October 25, 2026

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

https://huagongshe.com/reaction/54815

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CarbonateHCID 11430—
Reactant4-Nitrobenzyl chloroformateHCID 78205—
Reactant1-Amino-2,5-anhydro-1,3-dideoxy-6-O-[(1,1-dimethylethyl)diphenylsilyl]-D-arabino-hexitolHCID 67707376—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
Product2,5-Anhydro-1,3-dideoxy-6-O-[(1,1-dimethylethyl)diphenylsilyl]-1-[[[(4-nitrophenyl)methoxy]carbonyl]amino]-D-arabino-hexitolHCID 6770733175.6%

Reaction Conditions

Temperature0 °C

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05623081
Source datasetuspto-grants-1997_04
ORD IDord-3d69db3f9af84b3f86f427f7889047bb
Source noteuspto-grants-1997_04