Intermolecular aglycon transfer of ethyl thioglycosides can be prevented by judicious choice of protecting groups

Tong Zhu; Geert Jan Boons

doi:10.1016/S0008-6215(00)00252-4

Intermolecular aglycon transfer of ethyl thioglycosides can be prevented by judicious choice of protecting groups

Tong Zhu
, Geert Jan Boons^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

Unexpected intermolecular aglycon transfer occurred in chemoselective glycosylations using glycosyl fluorides or trichloroacetimidates as glycosyl donors and partially protected thioglycosides as glycosyl acceptors. It is shown that this problem can be addressed by fine-tuning of the reactivity of the anomeric thioalkyl moiety and hydroxyl of the acceptor.

Original language	English
Pages (from-to)	709-715
Number of pages	7
Journal	Carbohydrate Research
Volume	329
Issue number	4
DOIs	https://doi.org/10.1016/S0008-6215(00)00252-4
Publication status	Published - 1 Dec 2000
Externally published	Yes

Keywords

Chemoselective glycosylation
Lewis antigens
Oligosaccharide
Thioglycoside

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10.1016/S0008-6215(00)00252-4

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title = "Intermolecular aglycon transfer of ethyl thioglycosides can be prevented by judicious choice of protecting groups",

abstract = "Unexpected intermolecular aglycon transfer occurred in chemoselective glycosylations using glycosyl fluorides or trichloroacetimidates as glycosyl donors and partially protected thioglycosides as glycosyl acceptors. It is shown that this problem can be addressed by fine-tuning of the reactivity of the anomeric thioalkyl moiety and hydroxyl of the acceptor.",

keywords = "Chemoselective glycosylation, Lewis antigens, Oligosaccharide, Thioglycoside",

author = "Tong Zhu and Boons, \{Geert Jan\}",

year = "2000",

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doi = "10.1016/S0008-6215(00)00252-4",

language = "English",

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pages = "709--715",

journal = "Carbohydrate Research",

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TY - JOUR

T1 - Intermolecular aglycon transfer of ethyl thioglycosides can be prevented by judicious choice of protecting groups

AU - Zhu, Tong

AU - Boons, Geert Jan

PY - 2000/12/1

Y1 - 2000/12/1

N2 - Unexpected intermolecular aglycon transfer occurred in chemoselective glycosylations using glycosyl fluorides or trichloroacetimidates as glycosyl donors and partially protected thioglycosides as glycosyl acceptors. It is shown that this problem can be addressed by fine-tuning of the reactivity of the anomeric thioalkyl moiety and hydroxyl of the acceptor.

AB - Unexpected intermolecular aglycon transfer occurred in chemoselective glycosylations using glycosyl fluorides or trichloroacetimidates as glycosyl donors and partially protected thioglycosides as glycosyl acceptors. It is shown that this problem can be addressed by fine-tuning of the reactivity of the anomeric thioalkyl moiety and hydroxyl of the acceptor.

KW - Chemoselective glycosylation

KW - Lewis antigens

KW - Oligosaccharide

KW - Thioglycoside

U2 - 10.1016/S0008-6215(00)00252-4

DO - 10.1016/S0008-6215(00)00252-4

M3 - Article

C2 - 11125813

AN - SCOPUS:0034534544

SN - 0008-6215

VL - 329

SP - 709

EP - 715

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 4

ER -

Intermolecular aglycon transfer of ethyl thioglycosides can be prevented by judicious choice of protecting groups

Abstract

Keywords

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