Highly β-stereoselective glycosylation by use of 1-O-acetyl-2,6-anhydro-2-thio glycosyl donor for synthesis of 2,6-dideoxy-β-glycosides

Kazunobu Toshima; Yuko Nozaki; Satsuki Mukaiyama; Kuniaki Tatsuta

doi:10.1016/S0040-4039(00)91656-3

Highly β-stereoselective glycosylation by use of 1-O-acetyl-2,6-anhydro-2-thio glycosyl donor for synthesis of 2,6-dideoxy-β-glycosides

Kazunobu Toshima
, Yuko Nozaki
, Satsuki Mukaiyama
, Kuniaki Tatsuta

Department of Applied Chemistry

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

16 Citations (Scopus)

Abstract

Gycosylations of the 1-O-acetyl-2,6-anhydro-2-thio sugar 3 with alcohols in the presence of several Lewis acids in CH₂Cl₂ proceeded smoothly to give the corresponding β-O-glycosides with high stereocontrol in high yields, and the selectivity of the glycosylation was highly independent on Lewis acids.

Original language	English
Pages (from-to)	1491-1494
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	11
DOIs	https://doi.org/10.1016/S0040-4039(00)91656-3
Publication status	Published - 1992 Mar 10

Keywords

1-O-acetyl-2,6-anhydro-2-thio glycosyl donor
2,6-dideoxy glycoside
Lewis acid
thermodynamic control
β-stereoselective glycosylation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)91656-3

Cite this

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title = "Highly β-stereoselective glycosylation by use of 1-O-acetyl-2,6-anhydro-2-thio glycosyl donor for synthesis of 2,6-dideoxy-β-glycosides",

abstract = "Gycosylations of the 1-O-acetyl-2,6-anhydro-2-thio sugar 3 with alcohols in the presence of several Lewis acids in CH2Cl2 proceeded smoothly to give the corresponding β-O-glycosides with high stereocontrol in high yields, and the selectivity of the glycosylation was highly independent on Lewis acids.",

keywords = "1-O-acetyl-2,6-anhydro-2-thio glycosyl donor, 2,6-dideoxy glycoside, Lewis acid, thermodynamic control, β-stereoselective glycosylation",

author = "Kazunobu Toshima and Yuko Nozaki and Satsuki Mukaiyama and Kuniaki Tatsuta",

note = "Funding Information: We are grateful to the Instituteo f Microbial Chemistry for the generouss upporto f our program.F inancial supports by the Ministry of Education, Science and Culture (Grant-in-Aid Scientific Research) is gratefully acknowledged.",

year = "1992",

month = mar,

day = "10",

doi = "10.1016/S0040-4039(00)91656-3",

language = "English",

volume = "33",

pages = "1491--1494",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "11",

}

TY - JOUR

T1 - Highly β-stereoselective glycosylation by use of 1-O-acetyl-2,6-anhydro-2-thio glycosyl donor for synthesis of 2,6-dideoxy-β-glycosides

AU - Toshima, Kazunobu

AU - Nozaki, Yuko

AU - Mukaiyama, Satsuki

AU - Tatsuta, Kuniaki

N1 - Funding Information: We are grateful to the Instituteo f Microbial Chemistry for the generouss upporto f our program.F inancial supports by the Ministry of Education, Science and Culture (Grant-in-Aid Scientific Research) is gratefully acknowledged.

PY - 1992/3/10

Y1 - 1992/3/10

N2 - Gycosylations of the 1-O-acetyl-2,6-anhydro-2-thio sugar 3 with alcohols in the presence of several Lewis acids in CH2Cl2 proceeded smoothly to give the corresponding β-O-glycosides with high stereocontrol in high yields, and the selectivity of the glycosylation was highly independent on Lewis acids.

AB - Gycosylations of the 1-O-acetyl-2,6-anhydro-2-thio sugar 3 with alcohols in the presence of several Lewis acids in CH2Cl2 proceeded smoothly to give the corresponding β-O-glycosides with high stereocontrol in high yields, and the selectivity of the glycosylation was highly independent on Lewis acids.

KW - 1-O-acetyl-2,6-anhydro-2-thio glycosyl donor

KW - 2,6-dideoxy glycoside

KW - Lewis acid

KW - thermodynamic control

KW - β-stereoselective glycosylation

UR - https://www.scopus.com/pages/publications/0026511592

UR - https://www.scopus.com/pages/publications/0026511592#tab=citedBy

U2 - 10.1016/S0040-4039(00)91656-3

DO - 10.1016/S0040-4039(00)91656-3

M3 - Article

AN - SCOPUS:0026511592

SN - 0040-4039

VL - 33

SP - 1491

EP - 1494

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 11

ER -

Highly β-stereoselective glycosylation by use of 1-O-acetyl-2,6-anhydro-2-thio glycosyl donor for synthesis of 2,6-dideoxy-β-glycosides

Abstract

Keywords

ASJC Scopus subject areas

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