Stereoselective synthesis of 1,2-cis galactosides: synthesis of a glycolipid containing Galα1-6Gal component from Zygomycetes species

Noriyasu Hada; Junko Oka; Ayaka Nishiyama; Tadahiro Takeda

doi:10.1016/j.tetlet.2006.06.181

Stereoselective synthesis of 1,2-cis galactosides: synthesis of a glycolipid containing Galα1-6Gal component from Zygomycetes species

Noriyasu Hada, Junko Oka, Ayaka Nishiyama, Tadahiro Takeda

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

18 Citations (Scopus)

Abstract

An α-selective galactosylation was demonstrated under various conditions. Among these α-galactoside approaches, high α-selectivity was achieved by the virtue of 4,6-O-di-tert-butylsilylene (DTBS) group. Yield was further improved by the influence of a 2-O-benzylated donor compared to 2-O-benzoylated donor. This method was then applied to the first highly stereoselective synthesis of a newly found trisaccharide glycosphingolipid in Zygomycetes species.

Original language	English
Pages (from-to)	6647-6650
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	37
DOIs	https://doi.org/10.1016/j.tetlet.2006.06.181
Publication status	Published - 2006 Sept 11
Externally published	Yes

Keywords

1,2-cis-Glycoside
Di-tert-butylsilylene group
Zygomycetes species
d-Galactose
α-Galactosylation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.06.181

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title = "Stereoselective synthesis of 1,2-cis galactosides: synthesis of a glycolipid containing Galα1-6Gal component from Zygomycetes species",

abstract = "An α-selective galactosylation was demonstrated under various conditions. Among these α-galactoside approaches, high α-selectivity was achieved by the virtue of 4,6-O-di-tert-butylsilylene (DTBS) group. Yield was further improved by the influence of a 2-O-benzylated donor compared to 2-O-benzoylated donor. This method was then applied to the first highly stereoselective synthesis of a newly found trisaccharide glycosphingolipid in Zygomycetes species.",

keywords = "1,2-cis-Glycoside, Di-tert-butylsilylene group, Zygomycetes species, d-Galactose, α-Galactosylation",

author = "Noriyasu Hada and Junko Oka and Ayaka Nishiyama and Tadahiro Takeda",

note = "Funding Information: This work was supported under the High-Tech Research Center project of the Ministry of Education, Culture, Sports, Science and Technology of Japan. The authors are grateful to Ms. J. Hada for providing NMR and MS data.",

year = "2006",

month = sep,

day = "11",

doi = "10.1016/j.tetlet.2006.06.181",

language = "English",

volume = "47",

pages = "6647--6650",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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number = "37",

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TY - JOUR

T1 - Stereoselective synthesis of 1,2-cis galactosides

T2 - synthesis of a glycolipid containing Galα1-6Gal component from Zygomycetes species

AU - Hada, Noriyasu

AU - Oka, Junko

AU - Nishiyama, Ayaka

AU - Takeda, Tadahiro

N1 - Funding Information: This work was supported under the High-Tech Research Center project of the Ministry of Education, Culture, Sports, Science and Technology of Japan. The authors are grateful to Ms. J. Hada for providing NMR and MS data.

PY - 2006/9/11

Y1 - 2006/9/11

N2 - An α-selective galactosylation was demonstrated under various conditions. Among these α-galactoside approaches, high α-selectivity was achieved by the virtue of 4,6-O-di-tert-butylsilylene (DTBS) group. Yield was further improved by the influence of a 2-O-benzylated donor compared to 2-O-benzoylated donor. This method was then applied to the first highly stereoselective synthesis of a newly found trisaccharide glycosphingolipid in Zygomycetes species.

AB - An α-selective galactosylation was demonstrated under various conditions. Among these α-galactoside approaches, high α-selectivity was achieved by the virtue of 4,6-O-di-tert-butylsilylene (DTBS) group. Yield was further improved by the influence of a 2-O-benzylated donor compared to 2-O-benzoylated donor. This method was then applied to the first highly stereoselective synthesis of a newly found trisaccharide glycosphingolipid in Zygomycetes species.

KW - 1,2-cis-Glycoside

KW - Di-tert-butylsilylene group

KW - Zygomycetes species

KW - d-Galactose

KW - α-Galactosylation

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DO - 10.1016/j.tetlet.2006.06.181

M3 - Article

AN - SCOPUS:33746788505

SN - 0040-4039

VL - 47

SP - 6647

EP - 6650

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

Stereoselective synthesis of 1,2-cis galactosides: synthesis of a glycolipid containing Galα1-6Gal component from Zygomycetes species

Abstract

Keywords

ASJC Scopus subject areas

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