Armed-disarmed effect of remote protecting groups on the glycosylation reaction of 2,3-dideoxyglycosyl donors

Satoshi Tomono; Shunichi Kusumi; Daisuke Takahashi; Kazunobu Toshima

doi:10.1016/j.tetlet.2011.02.109

Armed-disarmed effect of remote protecting groups on the glycosylation reaction of 2,3-dideoxyglycosyl donors

Satoshi Tomono, Shunichi Kusumi, Daisuke Takahashi, Kazunobu Toshima

Department of Applied Chemistry

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

8 Citations (Scopus)

Abstract

The armed-disarmed effect of remote protecting groups at the C-4 and/or C-6 position(s) on the glycosylation reactions of 2,3-dideoxyglycosyl donors was investigated. It was found that under various glycosylation conditions, 4- or 6-O-Bn 2,3-dideoxyglycosyl donors were much more reactive than the corresponding 4,6-di-O-Bz 2,3-dideoxyglycosyl donors. Based on these results, an effective and chemoselective glycosylation reaction using 4,6-di-O-Bn glycosyl acetate and 4-OH-6-O-Bz glycosyl acetate was realized, producing a 2,3-dideoxydisaccharide in good yield with high α-stereoselectivity.

Original language	English
Pages (from-to)	2399-2403
Number of pages	5
Journal	Tetrahedron Letters
Volume	52
Issue number	18
DOIs	https://doi.org/10.1016/j.tetlet.2011.02.109
Publication status	Published - 2011 May 4

Keywords

2,3-Dideoxyglycosides
Armed-disarmed concept
Chemoselective glycosylation
Remote protecting group effect

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Armed-disarmed effect of remote protecting groups on the glycosylation reaction of 2,3-dideoxyglycosyl donors",

abstract = "The armed-disarmed effect of remote protecting groups at the C-4 and/or C-6 position(s) on the glycosylation reactions of 2,3-dideoxyglycosyl donors was investigated. It was found that under various glycosylation conditions, 4- or 6-O-Bn 2,3-dideoxyglycosyl donors were much more reactive than the corresponding 4,6-di-O-Bz 2,3-dideoxyglycosyl donors. Based on these results, an effective and chemoselective glycosylation reaction using 4,6-di-O-Bn glycosyl acetate and 4-OH-6-O-Bz glycosyl acetate was realized, producing a 2,3-dideoxydisaccharide in good yield with high α-stereoselectivity.",

keywords = "2,3-Dideoxyglycosides, Armed-disarmed concept, Chemoselective glycosylation, Remote protecting group effect",

author = "Satoshi Tomono and Shunichi Kusumi and Daisuke Takahashi and Kazunobu Toshima",

note = "Funding Information: This research was supported by the High-Tech Research Center Project for Private Universities: Matching Fund Subsidy, 2006–2011, from the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT). ",

year = "2011",

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doi = "10.1016/j.tetlet.2011.02.109",

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AU - Tomono, Satoshi

AU - Kusumi, Shunichi

AU - Takahashi, Daisuke

AU - Toshima, Kazunobu

N1 - Funding Information: This research was supported by the High-Tech Research Center Project for Private Universities: Matching Fund Subsidy, 2006–2011, from the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT).

PY - 2011/5/4

Y1 - 2011/5/4

N2 - The armed-disarmed effect of remote protecting groups at the C-4 and/or C-6 position(s) on the glycosylation reactions of 2,3-dideoxyglycosyl donors was investigated. It was found that under various glycosylation conditions, 4- or 6-O-Bn 2,3-dideoxyglycosyl donors were much more reactive than the corresponding 4,6-di-O-Bz 2,3-dideoxyglycosyl donors. Based on these results, an effective and chemoselective glycosylation reaction using 4,6-di-O-Bn glycosyl acetate and 4-OH-6-O-Bz glycosyl acetate was realized, producing a 2,3-dideoxydisaccharide in good yield with high α-stereoselectivity.

AB - The armed-disarmed effect of remote protecting groups at the C-4 and/or C-6 position(s) on the glycosylation reactions of 2,3-dideoxyglycosyl donors was investigated. It was found that under various glycosylation conditions, 4- or 6-O-Bn 2,3-dideoxyglycosyl donors were much more reactive than the corresponding 4,6-di-O-Bz 2,3-dideoxyglycosyl donors. Based on these results, an effective and chemoselective glycosylation reaction using 4,6-di-O-Bn glycosyl acetate and 4-OH-6-O-Bz glycosyl acetate was realized, producing a 2,3-dideoxydisaccharide in good yield with high α-stereoselectivity.

KW - 2,3-Dideoxyglycosides

KW - Armed-disarmed concept

KW - Chemoselective glycosylation

KW - Remote protecting group effect

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JF - Tetrahedron Letters

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Armed-disarmed effect of remote protecting groups on the glycosylation reaction of 2,3-dideoxyglycosyl donors

Abstract

Keywords

ASJC Scopus subject areas

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