Efficient Stereoselective Glycosylations of Alcohols by Sugar Perpivalates: The First Use of 1-O-Pivaloylated Glycosyl Donors

A.V. Pukin; H. Zuilhof

doi:10.1055/s-0029-1218361

Efficient Stereoselective Glycosylations of Alcohols by Sugar Perpivalates: The First Use of 1-O-Pivaloylated Glycosyl Donors

A.V. Pukin, H. Zuilhof

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

4 Citations (Scopus)

Abstract

1-O-Pivaloyl glycosides were shown to be efficient glycosyl donors by using the perpivaloylated derivatives of lactose, galactose and glucose in the direct ZnCl2-promoted glycosylations of various alcohols. The corresponding glycosides were isolated in good yields and ß-selectivity

Original language	English
Pages (from-to)	3267-3270
Journal	Synlett: accounts and rapid communications in synthetic organic chemistry
Volume	2009
Issue number	20
DOIs	https://doi.org/10.1055/s-0029-1218361
Publication status	Published - 2009

Keywords

natural-products synthesis
oligosaccharide synthesis
silicon surfaces
carbohydrate microarrays
o-glycosylation
glycolipids
strategies
tools
thioglycosides
analogs

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10.1055/s-0029-1218361

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title = "Efficient Stereoselective Glycosylations of Alcohols by Sugar Perpivalates: The First Use of 1-O-Pivaloylated Glycosyl Donors",

abstract = "1-O-Pivaloyl glycosides were shown to be efficient glycosyl donors by using the perpivaloylated derivatives of lactose, galactose and glucose in the direct ZnCl2-promoted glycosylations of various alcohols. The corresponding glycosides were isolated in good yields and {\ss}-selectivity",

keywords = "natural-products synthesis, oligosaccharide synthesis, silicon surfaces, carbohydrate microarrays, o-glycosylation, glycolipids, strategies, tools, thioglycosides, analogs",

author = "A.V. Pukin and H. Zuilhof",

year = "2009",

doi = "10.1055/s-0029-1218361",

language = "English",

volume = "2009",

pages = "3267--3270",

journal = "Synlett: accounts and rapid communications in synthetic organic chemistry",

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T1 - Efficient Stereoselective Glycosylations of Alcohols by Sugar Perpivalates: The First Use of 1-O-Pivaloylated Glycosyl Donors

AU - Pukin, A.V.

AU - Zuilhof, H.

PY - 2009

Y1 - 2009

N2 - 1-O-Pivaloyl glycosides were shown to be efficient glycosyl donors by using the perpivaloylated derivatives of lactose, galactose and glucose in the direct ZnCl2-promoted glycosylations of various alcohols. The corresponding glycosides were isolated in good yields and ß-selectivity

AB - 1-O-Pivaloyl glycosides were shown to be efficient glycosyl donors by using the perpivaloylated derivatives of lactose, galactose and glucose in the direct ZnCl2-promoted glycosylations of various alcohols. The corresponding glycosides were isolated in good yields and ß-selectivity

KW - natural-products synthesis

KW - oligosaccharide synthesis

KW - silicon surfaces

KW - carbohydrate microarrays

KW - o-glycosylation

KW - glycolipids

KW - strategies

KW - tools

KW - thioglycosides

KW - analogs

U2 - 10.1055/s-0029-1218361

DO - 10.1055/s-0029-1218361

M3 - Article

VL - 2009

SP - 3267

EP - 3270

JO - Synlett: accounts and rapid communications in synthetic organic chemistry

JF - Synlett: accounts and rapid communications in synthetic organic chemistry

SN - 0936-5214

IS - 20

ER -

Efficient Stereoselective Glycosylations of Alcohols by Sugar Perpivalates: The First Use of 1-O-Pivaloylated Glycosyl Donors

Abstract

Keywords

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