Chemistry of 1-methylenesugars: synthetic utilizations to 1'-C-methyl-saccharides and related carbohydrates

Rie Namme; Shiro Ikegami

doi:10.3987/REV-08-638

Chemistry of 1-methylenesugars: synthetic utilizations to 1'-C-methyl-saccharides and related carbohydrates

Rie Namme, Shiro Ikegami

Faculty of Pharmaceutical Sciences

Teikyo University

Research output: Contribution to journal › Review article › peer-review

2 Scopus citations

Abstract

The efficient synthesis of protected 1-methylenesugars and their acid-catalyzed O-glycosidation are mentioned in connection with that of 1-C-methyl-pyranoses. Application of this process to synthesis of the pentasaccharide PI-88 analogue was accomplished in a protected form. Also the syntheses of trehalose analogues and ulsonic acid derivatives were successful in the similar process. 1,3-Dipolar cycloaddition with nitrones provides the new types of spiro-heterocycles combined with carbohydrates. The closely related methylene-carbohydrates also provide a novel synthetic process for cyclitols that are useful synthetic intermediates for voglibose and related drugs.

Original language	English
Pages (from-to)	19-44
Number of pages	26
Journal	Heterocycles
Volume	78
Issue number	1
DOIs	https://doi.org/10.3987/REV-08-638
State	Published - 1 Jan 2009

Keywords

α-Glycosidation
1,3-Dipolar Cycloaddition
1-C-Methyltrehalose
1-Methylenesugar
spiro-Ketodisaccharide

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title = "Chemistry of 1-methylenesugars: synthetic utilizations to 1'-C-methyl-saccharides and related carbohydrates",

abstract = "The efficient synthesis of protected 1-methylenesugars and their acid-catalyzed O-glycosidation are mentioned in connection with that of 1-C-methyl-pyranoses. Application of this process to synthesis of the pentasaccharide PI-88 analogue was accomplished in a protected form. Also the syntheses of trehalose analogues and ulsonic acid derivatives were successful in the similar process. 1,3-Dipolar cycloaddition with nitrones provides the new types of spiro-heterocycles combined with carbohydrates. The closely related methylene-carbohydrates also provide a novel synthetic process for cyclitols that are useful synthetic intermediates for voglibose and related drugs.",

keywords = "α-Glycosidation, 1,3-Dipolar Cycloaddition, 1-C-Methyltrehalose, 1-Methylenesugar, spiro-Ketodisaccharide",

author = "Rie Namme and Shiro Ikegami",

year = "2009",

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day = "1",

doi = "10.3987/REV-08-638",

language = "英語",

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T1 - Chemistry of 1-methylenesugars

T2 - synthetic utilizations to 1'-C-methyl-saccharides and related carbohydrates

AU - Namme, Rie

AU - Ikegami, Shiro

PY - 2009/1/1

Y1 - 2009/1/1

N2 - The efficient synthesis of protected 1-methylenesugars and their acid-catalyzed O-glycosidation are mentioned in connection with that of 1-C-methyl-pyranoses. Application of this process to synthesis of the pentasaccharide PI-88 analogue was accomplished in a protected form. Also the syntheses of trehalose analogues and ulsonic acid derivatives were successful in the similar process. 1,3-Dipolar cycloaddition with nitrones provides the new types of spiro-heterocycles combined with carbohydrates. The closely related methylene-carbohydrates also provide a novel synthetic process for cyclitols that are useful synthetic intermediates for voglibose and related drugs.

AB - The efficient synthesis of protected 1-methylenesugars and their acid-catalyzed O-glycosidation are mentioned in connection with that of 1-C-methyl-pyranoses. Application of this process to synthesis of the pentasaccharide PI-88 analogue was accomplished in a protected form. Also the syntheses of trehalose analogues and ulsonic acid derivatives were successful in the similar process. 1,3-Dipolar cycloaddition with nitrones provides the new types of spiro-heterocycles combined with carbohydrates. The closely related methylene-carbohydrates also provide a novel synthetic process for cyclitols that are useful synthetic intermediates for voglibose and related drugs.

KW - α-Glycosidation

KW - 1,3-Dipolar Cycloaddition

KW - 1-C-Methyltrehalose

KW - 1-Methylenesugar

KW - spiro-Ketodisaccharide

UR - https://www.scopus.com/pages/publications/62549115717

U2 - 10.3987/REV-08-638

DO - 10.3987/REV-08-638

M3 - 総説

AN - SCOPUS:62549115717

SN - 0385-5414

VL - 78

SP - 19

EP - 44

JO - Heterocycles

JF - Heterocycles

IS - 1

ER -

Chemistry of 1-methylenesugars: synthetic utilizations to 1'-C-methyl-saccharides and related carbohydrates

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Keywords

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