HCID 53802815, compound → HCID 54288094, compound

HRID 1157055Notes

Reaction equation

HRID 1157055 reaction equation
[C@H:1]1([O:12][C@@H:13]2[C@@H:18]([CH2:19][OH:20])[O:17][C@@H:16]([N:21]=[N+]=[N-])[C@H:15]([OH:24])[C@H:14]2[OH:25])[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]>O1CCOC(CCN)C1(CCN)CCN.[Pd]>[C@H:1]1([O:12][C@@H:13]2[C@@H:18]([CH2:19][OH:20])[O:17][C@@H:16]([NH2:21])[C@H:15]([OH:24])[C@H:14]2[OH:25])[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 1

HCID 53802815HCID 53802815, compound

Product 1

HCID 54288094HCID 54288094, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 67841075HCID 67841075, compoundSolvent

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. customThe product is crystallized from dioxane-ethanol

Sources & evidence

ORD record
ord-1b1f49c0472a4841b3f0d6e8e8b44c12
Source dataset
uspto-grants-1982_06
Patent number
US04337249

Reaction notes

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