Sodium Azide → 2,3,4-Tri-O-acetyl-beta-D-fucopyranosyl azide

HRID 1292414Notes

Reaction equation

HRID 1292414 reaction equation
[N-]=[N+]=[N-].[Na+].C(N[C@@H:9]1[C@@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@H:13]([O:19][C:20](=[O:22])[CH3:21])[C@@H:12]([CH2:23]OC(=O)C)[O:11][C@H:10]1[N:28]=[N+:29]=[N-:30])(=O)C>CN(C)C=O>[C:16]([O:18][C@@H:9]1[C@@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@@H:13]([O:19][C:20](=[O:22])[CH3:21])[C@@H:12]([CH3:23])[O:11][C@H:10]1[N:28]=[N+:29]=[N-:30])(=[O:15])[CH3:17]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 2725015beta-D-Glucopyranosyl azide, 2-(acetylamino)-2-deoxy-, 3,4,6-triacetate

Product 1

HCID 228505752,3,4-Tri-O-acetyl-beta-D-fucopyranosyl azide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of diphenyl(2,3,4-tri-O-acetyl-α-D-fucopyranosyl)-phosphate (2.0 g) in anhydrous dimethylformamide (80 mL) containing sodium azide (2.0 g) was heated to 50° C. for 2 h and processed as described in the synthesis of Compound 5, part c (Experiment 4). The product was purified by chromatography on a column of silica gel using ethyl acetate--hexane (3:8) as eluant to obtain the title compound (1.13 g).

Workup

  1. customThe product was purified by chromatography on a column of silica gel

Sources & evidence

ORD record
ord-d681730568c44767b172102a4763fcfb
Source dataset
uspto-grants-1998_05
Patent number
US05756712

Reaction notes

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