D-Galactosamine → N-Acetyl-D-Galactosamine

HRID 1660559Notes

Reaction equation

[N:1]([C@H:4]([C@H:7]([C@H:9]([C@@H:11]([CH2:13][OH:14])[OH:12])[OH:10])[OH:8])[CH:5]=[O:6])=[N+]=[N-].[OH:15][CH:16]1O[C@H](CO)[C@H](O)[C@H](O)[C@H:17]1N>>[C:16]([NH:1][C@@H:4]1[C@@H:7]([OH:8])[C@@H:9]([OH:10])[C@@H:11]([CH2:13][OH:14])[O:12][CH:5]1[OH:6])(=[O:15])[CH3:17]

Participants

Reactant 2

HCID 24154D-Galactosamine

HCID 228620522-Azido-2-deoxy-D-galactose

Product 1

HCID 35717N-Acetyl-D-Galactosamine

Procedure

The process which comprises reacting an anomeric mixture of 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl nitrate with sodium acetate in acetic acid to form the 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl acetates, isolating said product, hydrolyzing said isolated product in an aqueous acid to provide 2-azido-2-deoxy-D-galactose, and reducing the 2-azido-2-deoxy-D-galactose and then N-acetylating the D-galactosamine product to form N-acetyl-D-galactosamine.

Sources & evidence

ORD record: ord-b6533c0c126a449e9b467a3646296df9
Source dataset: uspto-grants-1981_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04308376

Reaction notes

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