Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates.

Santanu Mandal; Ulf Nilsson

doi:10.1039/c4ob00741g

Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates.

Santanu Mandal, Ulf Nilsson

Centre for Analysis and Synthesis

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

Abstract

Tri-isopropylsilyl thio-glycosides (TIPS S-glycosides) were synthesized through base promoted SN2 substitution of glycosyl halides with TIPS-SH or by Lewis acid promoted glycosylation of TIPS-SH with glycosyl acetates or p-methoxyphenyl glycosides. Various thioglycoside derivatives were obtained in high yields by one-pot fluoride-mediated de-silylation and thiol alkylation with alkyl halides or Michael acceptors of one common TIPS S-glycoside.

Original language	English
Pages (from-to)	4816-4819
Journal	Organic and Biomolecular Chemistry
Volume	12
Issue number	27
DOIs	https://doi.org/10.1039/c4ob00741g
Publication status	Published - 2014

Subject classification (UKÄ)

Chemical Sciences

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10.1039/c4ob00741g

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title = "Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates.",

abstract = "Tri-isopropylsilyl thio-glycosides (TIPS S-glycosides) were synthesized through base promoted SN2 substitution of glycosyl halides with TIPS-SH or by Lewis acid promoted glycosylation of TIPS-SH with glycosyl acetates or p-methoxyphenyl glycosides. Various thioglycoside derivatives were obtained in high yields by one-pot fluoride-mediated de-silylation and thiol alkylation with alkyl halides or Michael acceptors of one common TIPS S-glycoside.",

author = "Santanu Mandal and Ulf Nilsson",

year = "2014",

doi = "10.1039/c4ob00741g",

language = "English",

volume = "12",

pages = "4816--4819",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0539",

publisher = "Royal Society of Chemistry",

number = "27",

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T1 - Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates.

AU - Mandal, Santanu

AU - Nilsson, Ulf

PY - 2014

Y1 - 2014

N2 - Tri-isopropylsilyl thio-glycosides (TIPS S-glycosides) were synthesized through base promoted SN2 substitution of glycosyl halides with TIPS-SH or by Lewis acid promoted glycosylation of TIPS-SH with glycosyl acetates or p-methoxyphenyl glycosides. Various thioglycoside derivatives were obtained in high yields by one-pot fluoride-mediated de-silylation and thiol alkylation with alkyl halides or Michael acceptors of one common TIPS S-glycoside.

AB - Tri-isopropylsilyl thio-glycosides (TIPS S-glycosides) were synthesized through base promoted SN2 substitution of glycosyl halides with TIPS-SH or by Lewis acid promoted glycosylation of TIPS-SH with glycosyl acetates or p-methoxyphenyl glycosides. Various thioglycoside derivatives were obtained in high yields by one-pot fluoride-mediated de-silylation and thiol alkylation with alkyl halides or Michael acceptors of one common TIPS S-glycoside.

U2 - 10.1039/c4ob00741g

DO - 10.1039/c4ob00741g

M3 - Article

C2 - 24867410

SN - 1477-0539

VL - 12

SP - 4816

EP - 4819

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 27

ER -

Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates.

Abstract

Subject classification (UKÄ)

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