Synthesis of O-glycopyranosyl-N-hydroxysuccinimides of glucose and lactose and their opening by nucleophiles into prespacer glycosides.

Abstract:

:O-Glycopyranosyl-N-hydroxysuccinimides of glucose and lactose have been synthesized. Peracetylated sugars, acetobromo sugars and benzoylated thioethyl glycosides have been used as precursors. With boron trifluoride etherate in dichloromethane, peracetylated sugars gave predominantly the beta anomer. Trimethylsilyl trifluoromethanesulfonate in nitromethane, however, gave predominantly the alpha anomer. Treatment of the acetylated O-glucopyranosyl-N-hydroxysuccinimide with various nucleophiles (methoxide, hydroxide and pentylamine) gave the corresponding deacetylated N-(succinyl)glucopyranosylhydroxylamines in almost quantitative yield. These derivatives are suitable for the formation of glycoconjugates or attachment of carbohydrates to solid phases using the opened succinimide as linking arm.

journal_name

Glycoconj J

journal_title

Glycoconjugate journal

authors

Andersson M,Oscarson S

doi

10.1007/BF00780758

subject

Has Abstract

pub_date

1992-06-01 00:00:00

pages

122-5

issue

3

eissn

0282-0080

issn

1573-4986

journal_volume

9

pub_type

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