Sodium Azide → HCID 53802815, compound

HRID 1157054Notes

Reaction equation

HRID 1157054 reaction equation
[C@H:1]1([O:12][C@@H:13]2[C@@H:18]([CH2:19][OH:20])[O:17][C@@H:16](Br)[C@H:15]([OH:22])[C@H:14]2[OH:23])[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].[N-:24]=[N+:25]=[N-:26].[Na+]>CS(C)=O>[C@H:1]1([O:12][C@@H:13]2[C@@H:18]([CH2:19][OH:20])[O:17][C@@H:16]([N:24]=[N+:25]=[N-:26])[C@H:15]([OH:22])[C@H:14]2[OH:23])[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 54203883HCID 54203883, compound

Product 1

HCID 53802815HCID 53802815, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-O-α-D-glucopyranosyl-β-D-glucopyranosyl bromide, heptaacetate (4) is reacted with sodium azide in dimethylsulfoxide at 55°-65° C. for 10-30 minutes followed by extraction in organic solvents, giving 4-O-α-D-glucopyranosyl-β-D-glucopyranosylazide, heptaacetate (6). The azide is hydrogenated at room temperature under pressure in dioxane-triethylamine solution using 10% palladium on carbon catalyst. The product is crystallized from dioxane-ethanol to provide 4-O-α-D-glucopyranosyl-β-D-glucopyranosylamine, heptaacetate (heptaester).

Workup

  1. extractionfollowed by extraction in organic solvents

Sources & evidence

ORD record
ord-3597a3ad668e49da8225e76d687f9525
Source dataset
uspto-grants-1982_06
Patent number
US04337249

Reaction notes

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