Water → ST50306943

HRID 477580Notes

Reaction equation

[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][O:7][C@@H:6]1Br)(=[O:3])[CH3:2].[N-:20]=[N+:21]=[N-:22].[Na+].O>C(#N)C>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][O:7][C@H:6]1[N:20]=[N+:21]=[N-:22])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

In acetonitrile was dissolved 3 g of 2,3,4-tri-O-acetyl-α-D-xylopyranosyl bromide, and 2.88 g of dry sodium azide was added to the solution. The mixture was stirred at 60° C. for 4 hours. Water was added to the reaction and the mixture was extracted with chloroform. The chloroform layer was washed with water, dehydrated and subjected to silica gel column chromatography with a solvent system of chloroform-acetone (100:1) to obtain 1.36 g of 2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-xylopyranose.

Workup

additionwas added to the solution
extractionthe mixture was extracted with chloroform
washThe chloroform layer was washed with water

Sources & evidence

ORD record: ord-1000d8fec0a740e1a4908e9f17691dcd
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04888418

Reaction notes

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