Highly β-selective mannosylation towards Manβ1-4GlcNAc synthesis: TMSB(C6F5)4 as a Lewis acid/cation trap catalyst

Shin Ichi Tanaka; Mamoru Takashina; Hiroomi Tokimoto; Yukari Fujimoto; Katsunori Tanaka; Koichi Fukase

doi:10.1055/s-2005-872678

Highly β-selective mannosylation towards Manβ1-4GlcNAc synthesis: TMSB(C₆F₅)₄ as a Lewis acid/cation trap catalyst

Shin Ichi Tanaka, Mamoru Takashina, Hiroomi Tokimoto, Yukari Fujimoto, Katsunori Tanaka, Koichi Fukase

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

64 Citations (Scopus)

Abstract

Highly β-selective mannosylation of 4,6-0-benzylidene-mannopyranosyl- N-phenyltrifluoroacetimidate (α/β, 5:95, 93% yield) has been realized by utilizing a dual Lewis acid/cation trap catalyst, TMSB(C₆F ₅)₄. The obtained Manβ1-4GlcNTroc unit can be readily converted to a variety of N-linked oligosaccharides.

Original language	English
Pages (from-to)	2325-2328
Number of pages	4
Journal	Synlett
Issue number	15
DOIs	https://doi.org/10.1055/s-2005-872678
Publication status	Published - 2005 Sept 19
Externally published	Yes

Keywords

Lewis acid
Manβ1-4GlcNAc synthesis
Oligosaccharides
Stereoselective mannosylation
TMSB(CF)
β-glycoside

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1055/s-2005-872678

Cite this

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title = "Highly β-selective mannosylation towards Manβ1-4GlcNAc synthesis: TMSB(C6F5)4 as a Lewis acid/cation trap catalyst",

abstract = "Highly β-selective mannosylation of 4,6-0-benzylidene-mannopyranosyl- N-phenyltrifluoroacetimidate (α/β, 5:95, 93% yield) has been realized by utilizing a dual Lewis acid/cation trap catalyst, TMSB(C6F 5)4. The obtained Manβ1-4GlcNTroc unit can be readily converted to a variety of N-linked oligosaccharides.",

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author = "Tanaka, {Shin Ichi} and Mamoru Takashina and Hiroomi Tokimoto and Yukari Fujimoto and Katsunori Tanaka and Koichi Fukase",

year = "2005",

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doi = "10.1055/s-2005-872678",

language = "English",

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T1 - Highly β-selective mannosylation towards Manβ1-4GlcNAc synthesis

T2 - TMSB(C6F5)4 as a Lewis acid/cation trap catalyst

AU - Tanaka, Shin Ichi

AU - Takashina, Mamoru

AU - Tokimoto, Hiroomi

AU - Fujimoto, Yukari

AU - Tanaka, Katsunori

AU - Fukase, Koichi

PY - 2005/9/19

Y1 - 2005/9/19

N2 - Highly β-selective mannosylation of 4,6-0-benzylidene-mannopyranosyl- N-phenyltrifluoroacetimidate (α/β, 5:95, 93% yield) has been realized by utilizing a dual Lewis acid/cation trap catalyst, TMSB(C6F 5)4. The obtained Manβ1-4GlcNTroc unit can be readily converted to a variety of N-linked oligosaccharides.

AB - Highly β-selective mannosylation of 4,6-0-benzylidene-mannopyranosyl- N-phenyltrifluoroacetimidate (α/β, 5:95, 93% yield) has been realized by utilizing a dual Lewis acid/cation trap catalyst, TMSB(C6F 5)4. The obtained Manβ1-4GlcNTroc unit can be readily converted to a variety of N-linked oligosaccharides.

KW - Lewis acid

KW - Manβ1-4GlcNAc synthesis

KW - Oligosaccharides

KW - Stereoselective mannosylation

KW - TMSB(CF)

KW - β-glycoside

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