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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 54812Generated: October 26, 2026

Lithium azide → 2,5-Anhydro-6-azido-4,6-dideoxy-1-O-[(1,1-dimethylethyl)diphenylsilyl]-D-arabino-hexitol

https://huagongshe.com/reaction/54812

Reaction equation

Participants

RoleNameHCIDCharge
ReactantLithium azideHCID 88163—
Reactant2,5-Anhydro-4,6-dideoxy-1-O-[(1,1-dimethylethyl)diphenylsilyl]-6-iodo-D-arabino-hexitolHCID 67707319—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product2,5-Anhydro-6-azido-4,6-dideoxy-1-O-[(1,1-dimethylethyl)diphenylsilyl]-D-arabino-hexitolHCID 8675035196.5%

Reaction Conditions

Temperature80 °C

Reaction Steps

A solution, under argon, of 5.0 g of product from Example 275 in 10 ml of dry N,N-dimethylformamide is treated with 0.986 g of lithium azide. The minute is stirred at 80° C. for 1 hour followed by room temperature for 18 hours. The reaction is diluted with water, extracted with diethyl ether, concentrated in vacuo, purified by chromatography (silica gel: 5-50% ethyl acetate/hexane) to give 4.0 g of the desired product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05623081
Source datasetuspto-grants-1997_04
ORD IDord-8f8b0776df724f59ab01c2e9a34d6605
Source noteuspto-grants-1997_04