Efficient and stereoselective synthesis of the disaccharide fragment of incednine

Takashi Ohtani; Shohei Sakai; Akira Takada; Daisuke Takahashi; Kazunobu Toshima

doi:10.1021/ol202639v

Efficient and stereoselective synthesis of the disaccharide fragment of incednine

Takashi Ohtani, Shohei Sakai, Akira Takada, Daisuke Takahashi, Kazunobu Toshima

Department of Applied Chemistry

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

8 Citations (Scopus)

Abstract

Efficient and stereoselective synthesis of a disaccharide fragment, 2-deoxy-4-O-(N′-monodemethyl-d-forosaminyl)-2-methylamino-β-d- xylopyranoside, of a novel antibiotic, incednine (1), is described. The key β-stereoselective formation of a 2,3,4,6-tetradeoxy-4-methylamino glycoside bond was achieved by remote participation-assisted glycosylation.

Original language	English
Pages (from-to)	6126-6129
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	22
DOIs	https://doi.org/10.1021/ol202639v
Publication status	Published - 2011 Nov 18

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol202639v

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abstract = "Efficient and stereoselective synthesis of a disaccharide fragment, 2-deoxy-4-O-(N′-monodemethyl-d-forosaminyl)-2-methylamino-β-d- xylopyranoside, of a novel antibiotic, incednine (1), is described. The key β-stereoselective formation of a 2,3,4,6-tetradeoxy-4-methylamino glycoside bond was achieved by remote participation-assisted glycosylation.",

author = "Takashi Ohtani and Shohei Sakai and Akira Takada and Daisuke Takahashi and Kazunobu Toshima",

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AU - Ohtani, Takashi

AU - Sakai, Shohei

AU - Takada, Akira

AU - Takahashi, Daisuke

AU - Toshima, Kazunobu

PY - 2011/11/18

Y1 - 2011/11/18

N2 - Efficient and stereoselective synthesis of a disaccharide fragment, 2-deoxy-4-O-(N′-monodemethyl-d-forosaminyl)-2-methylamino-β-d- xylopyranoside, of a novel antibiotic, incednine (1), is described. The key β-stereoselective formation of a 2,3,4,6-tetradeoxy-4-methylamino glycoside bond was achieved by remote participation-assisted glycosylation.

AB - Efficient and stereoselective synthesis of a disaccharide fragment, 2-deoxy-4-O-(N′-monodemethyl-d-forosaminyl)-2-methylamino-β-d- xylopyranoside, of a novel antibiotic, incednine (1), is described. The key β-stereoselective formation of a 2,3,4,6-tetradeoxy-4-methylamino glycoside bond was achieved by remote participation-assisted glycosylation.

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JO - Organic Letters

JF - Organic Letters

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Efficient and stereoselective synthesis of the disaccharide fragment of incednine

Abstract

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