Glycosidation of solid-supported glycosyl donors tethered by a trialkylsilane linker

Takayuki Doi; Masayuki Sugiki; Haruo Yamada; Takashi Takahashi; John A. Porco

doi:10.1016/S0040-4039(99)00133-1

Glycosidation of solid-supported glycosyl donors tethered by a trialkylsilane linker

Takayuki Doi, Masayuki Sugiki, Haruo Yamada, Takashi Takahashi, John A. Porco

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

22 Citations (Scopus)

Abstract

Glycosidation of silicon-connected glycosyl donors on polystyrene resin is described Thiophenyl glycoside 2a and glucopyranosyl fluoride 2b reacted with glycosyl acceptor 3 (R² = Bn) to give disaccharide 4a in 96% and 70% yields, respectively. Glycosidation of thiophenyl glucoside 2a (R¹ = Bn or Bz) with glycosyl acceptor 3 (R² = Bn or Ac) yielded 4a-4c in satisfactory yields and 4d in moderate yield.

Original language	English
Pages (from-to)	2141-2144
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	11
DOIs	https://doi.org/10.1016/S0040-4039(99)00133-1
Publication status	Published - 1999 Mar 12
Externally published	Yes

Keywords

Glycosidation
Resins
Solid-phase synthesis
Thioglycosides

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(99)00133-1

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title = "Glycosidation of solid-supported glycosyl donors tethered by a trialkylsilane linker",

abstract = "Glycosidation of silicon-connected glycosyl donors on polystyrene resin is described Thiophenyl glycoside 2a and glucopyranosyl fluoride 2b reacted with glycosyl acceptor 3 (R2 = Bn) to give disaccharide 4a in 96% and 70% yields, respectively. Glycosidation of thiophenyl glucoside 2a (R1 = Bn or Bz) with glycosyl acceptor 3 (R2 = Bn or Ac) yielded 4a-4c in satisfactory yields and 4d in moderate yield.",

keywords = "Glycosidation, Resins, Solid-phase synthesis, Thioglycosides",

author = "Takayuki Doi and Masayuki Sugiki and Haruo Yamada and Takashi Takahashi and Porco, {John A.}",

year = "1999",

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T1 - Glycosidation of solid-supported glycosyl donors tethered by a trialkylsilane linker

AU - Doi, Takayuki

AU - Sugiki, Masayuki

AU - Yamada, Haruo

AU - Takahashi, Takashi

AU - Porco, John A.

PY - 1999/3/12

Y1 - 1999/3/12

N2 - Glycosidation of silicon-connected glycosyl donors on polystyrene resin is described Thiophenyl glycoside 2a and glucopyranosyl fluoride 2b reacted with glycosyl acceptor 3 (R2 = Bn) to give disaccharide 4a in 96% and 70% yields, respectively. Glycosidation of thiophenyl glucoside 2a (R1 = Bn or Bz) with glycosyl acceptor 3 (R2 = Bn or Ac) yielded 4a-4c in satisfactory yields and 4d in moderate yield.

AB - Glycosidation of silicon-connected glycosyl donors on polystyrene resin is described Thiophenyl glycoside 2a and glucopyranosyl fluoride 2b reacted with glycosyl acceptor 3 (R2 = Bn) to give disaccharide 4a in 96% and 70% yields, respectively. Glycosidation of thiophenyl glucoside 2a (R1 = Bn or Bz) with glycosyl acceptor 3 (R2 = Bn or Ac) yielded 4a-4c in satisfactory yields and 4d in moderate yield.

KW - Glycosidation

KW - Resins

KW - Solid-phase synthesis

KW - Thioglycosides

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U2 - 10.1016/S0040-4039(99)00133-1

DO - 10.1016/S0040-4039(99)00133-1

M3 - Article

AN - SCOPUS:0033548435

SN - 0040-4039

VL - 40

SP - 2141

EP - 2144

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 11

ER -

Glycosidation of solid-supported glycosyl donors tethered by a trialkylsilane linker

Abstract

Keywords

ASJC Scopus subject areas

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