Synthesis of glycosides of 2,6-dimethyl-3,5-dichloro-4-pyridinol

Abstract

Three acetyl glycosides 1-O-(2',6'-dimethyl-3',5'-dichloro-4'-pyridyl)-2,3,4,6-tetra-O-acetyl-b-D-g alactopyranoside and Me 1-O-(2',6'-dimethyl-3',5'-dichloro-4'-pyridyl)-2,3,4-tri-O-acetyl-b-D-glucop yranuronate (I) were synthesized from 2,6-dimethyl-3,5-dichloro-4-pyridinol and relevant glycosyl bromide in the presence of phase transfer catalyst. The glycosides were treated with ammonia in methanol to obtain the corresponding 1-O-(2',6'-dimethyl-3',5'-dichloro-4'-pyridyl)-b-D-glucopyranoside, 1-O-(2',6'-dimethyl-3',5'-dichloro-4'-pyridyl)-b-D-galactopyranoside and 1-O-(2',6'-dimethyl-3',5'-dichloro-4'-pyridyl)-b-D-glucopyranuronamide resp. I was treated with sodium methoxide in methanol to obtain Me 1-O-(2',6'-dimethyl-3',5'-dichloro-4'-pyridyl)-b-D-glucopyranuronate.

Key words: PHASE TRANSFER CATALYSIS, GLYCOSIDE, PYRIDINOL P

CLC Number:

O621

Cite this article

CHEN ZAICHENG;SUN CHANGJUN;HU WEIFENG. Synthesis of glycosides of 2,6-dimethyl-3,5-dichloro-4-pyridinol[J]. Chin. J. Org. Chem., 1992, 12(3): 269-272.

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