Work

Studies of Aminosugars. XIX. Syntheses of O-Benzyl-α-halogeno Derivatives of 3-Acetamido-3-deoxy- and 6-Acetamido-6-deoxy- d -glucose

Year: 1968

Type: article

Abstract: As a part of investigation of the synthesis and reaction of 1-halogeno derivatives of amino-monosaccharides, 3-acetamido-2,4,6-tri-O-benzyl-3-deoxy-α-d-glucopyranosyl chloride and 2,3,4-tri-O-benzyl-6-(N-benzylacetamido)-6-deoxy-α-d-glucopyranosyl chloride have been synthesized. Attempts to prepare α-glycosides from these benzyl derivatives proved to be practical, giving cyclohexyl 3-acetamido-2,4,6-tri-O-benzyl-3-deoxy-α-d-glucopyranoside and cyclohexyl 2,3,4-tri-O-benzyl-6-(N-benzylacetamido)-6-deoxy-α-d-glucopyranoside as main products. Removal of the masking groups gave cyclohexyl α-glucosides of 3-amino-3-deoxy-d- and 6-amino-6-deoxy-d-glucose respectively. A number of related derivatives have been described.

Source: Bulletin of the Chemical Society of Japan

DOI: 10.1246/bcsj.41.2765

Authors: Shinkiti Koto, Takayuki Tsumura, Yoshinori Kato, Sumio Umezawa

Institution: Keio University

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

OpenAlex ID: W2125382387

FWCI: 2.566

Cites: 2

Cited by: 19

Related to: 10