First protection-free protocol for synthesis of 1-deoxy sugars through glycosyl dithiocarbamate intermediates

Gefei Li; Masato Noguchi; Kensuke Nakamura; Ryohei Hayasaka; Yuuki Tanaka; Shin ichiro Shoda

doi:10.1016/j.tetlet.2018.08.005

First protection-free protocol for synthesis of 1-deoxy sugars through glycosyl dithiocarbamate intermediates

Gefei Li, Masato Noguchi, Kensuke Nakamura, Ryohei Hayasaka, Yuuki Tanaka, Shin ichiro Shoda

ENG - Biomolecular Engineering

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

2 Citations (Scopus)

Abstract

A practical two-step synthetic process for 1-deoxy sugars has been established. The process consists of the direct introduction of a dimethyldithiocarbamate group into the anomeric center of unprotected sugars and subsequent hydrogenation in the AIBN-H₃PO₂-NaHCO₃ system. No protecting groups are needed to synthesize 1-deoxy monosaccharides and 1-deoxy disaccharides.

Original language	English
Pages (from-to)	3428-3431
Number of pages	4
Journal	Tetrahedron Letters
Volume	59
Issue number	37
DOIs	https://doi.org/10.1016/j.tetlet.2018.08.005
Publication status	Published - 2018 Sep 12

Keywords

1-Deoxy sugar
Direct anomeric activation
Glycosyl dithiocarbamate
Protection-free synthesis
Radical desulfurization

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "First protection-free protocol for synthesis of 1-deoxy sugars through glycosyl dithiocarbamate intermediates",

abstract = "A practical two-step synthetic process for 1-deoxy sugars has been established. The process consists of the direct introduction of a dimethyldithiocarbamate group into the anomeric center of unprotected sugars and subsequent hydrogenation in the AIBN-H3PO2-NaHCO3 system. No protecting groups are needed to synthesize 1-deoxy monosaccharides and 1-deoxy disaccharides.",

keywords = "1-Deoxy sugar, Direct anomeric activation, Glycosyl dithiocarbamate, Protection-free synthesis, Radical desulfurization",

author = "Gefei Li and Masato Noguchi and Kensuke Nakamura and Ryohei Hayasaka and Yuuki Tanaka and Shoda, {Shin ichiro}",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology , Japan. We thank Mr. Keisuke Hokotate for experimental support. Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

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doi = "10.1016/j.tetlet.2018.08.005",

language = "English",

volume = "59",

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TY - JOUR

T1 - First protection-free protocol for synthesis of 1-deoxy sugars through glycosyl dithiocarbamate intermediates

AU - Li, Gefei

AU - Noguchi, Masato

AU - Nakamura, Kensuke

AU - Hayasaka, Ryohei

AU - Tanaka, Yuuki

AU - Shoda, Shin ichiro

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology , Japan. We thank Mr. Keisuke Hokotate for experimental support. Publisher Copyright: © 2018 Elsevier Ltd

PY - 2018/9/12

Y1 - 2018/9/12

N2 - A practical two-step synthetic process for 1-deoxy sugars has been established. The process consists of the direct introduction of a dimethyldithiocarbamate group into the anomeric center of unprotected sugars and subsequent hydrogenation in the AIBN-H3PO2-NaHCO3 system. No protecting groups are needed to synthesize 1-deoxy monosaccharides and 1-deoxy disaccharides.

AB - A practical two-step synthetic process for 1-deoxy sugars has been established. The process consists of the direct introduction of a dimethyldithiocarbamate group into the anomeric center of unprotected sugars and subsequent hydrogenation in the AIBN-H3PO2-NaHCO3 system. No protecting groups are needed to synthesize 1-deoxy monosaccharides and 1-deoxy disaccharides.

KW - 1-Deoxy sugar

KW - Direct anomeric activation

KW - Glycosyl dithiocarbamate

KW - Protection-free synthesis

KW - Radical desulfurization

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DO - 10.1016/j.tetlet.2018.08.005

M3 - Article

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VL - 59

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EP - 3431

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 37

ER -

First protection-free protocol for synthesis of 1-deoxy sugars through glycosyl dithiocarbamate intermediates

Abstract

Keywords

ASJC Scopus subject areas

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