Convergent Synthesis of Digalactosyl Diacylglycerols

Shinsuke Inuki; Junichiro Kishi; Emi Kashiwabara; Toshihiko Aiba; Yukari Fujimoto

doi:10.1021/acs.orglett.7b03043

Convergent Synthesis of Digalactosyl Diacylglycerols

Shinsuke Inuki, Junichiro Kishi, Emi Kashiwabara, Toshihiko Aiba, Yukari Fujimoto

Department of Chemistry

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

3 Citations (Scopus)

Abstract

Efficient convergent chemical syntheses of digalactosyl diacylglycerols (DGDGs), which have both a galactose-galactose α(1→6)-linkage and a galactose-glycerol β-linkage along with a diacylglycerol containing various kinds of fatty acids, have been accomplished. In order to achieve a concise synthesis, we chose to use allylic protective groups as permanent protective groups. We have also achieved α- and β-selective glycosylations for the respective linkages with high yields as the key steps.

Original language	English
Pages (from-to)	6482-6485
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	24
DOIs	https://doi.org/10.1021/acs.orglett.7b03043
Publication status	Published - 2017 Dec 15

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Convergent Synthesis of Digalactosyl Diacylglycerols",

abstract = "Efficient convergent chemical syntheses of digalactosyl diacylglycerols (DGDGs), which have both a galactose-galactose α(1→6)-linkage and a galactose-glycerol β-linkage along with a diacylglycerol containing various kinds of fatty acids, have been accomplished. In order to achieve a concise synthesis, we chose to use allylic protective groups as permanent protective groups. We have also achieved α- and β-selective glycosylations for the respective linkages with high yields as the key steps.",

author = "Shinsuke Inuki and Junichiro Kishi and Emi Kashiwabara and Toshihiko Aiba and Yukari Fujimoto",

note = "Funding Information: We thank Prof. K. Suenaga for the assistance in measuring physical data of a compound. This research was supported by grants from the Grant-in-Aid for Scientific Research (Nos. JP26282211, JP26102732, JP26882036, JP17H02207, JP17H05800, JP16H01162, and JP16K16638), the Mizutani Foundation for Glycoscience, Mishima Kaiun Memorial Foundation, Takeda Science Foundation, and Protein Research Foundation. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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T1 - Convergent Synthesis of Digalactosyl Diacylglycerols

AU - Inuki, Shinsuke

AU - Kishi, Junichiro

AU - Kashiwabara, Emi

AU - Aiba, Toshihiko

AU - Fujimoto, Yukari

N1 - Funding Information: We thank Prof. K. Suenaga for the assistance in measuring physical data of a compound. This research was supported by grants from the Grant-in-Aid for Scientific Research (Nos. JP26282211, JP26102732, JP26882036, JP17H02207, JP17H05800, JP16H01162, and JP16K16638), the Mizutani Foundation for Glycoscience, Mishima Kaiun Memorial Foundation, Takeda Science Foundation, and Protein Research Foundation. Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/12/15

Y1 - 2017/12/15

N2 - Efficient convergent chemical syntheses of digalactosyl diacylglycerols (DGDGs), which have both a galactose-galactose α(1→6)-linkage and a galactose-glycerol β-linkage along with a diacylglycerol containing various kinds of fatty acids, have been accomplished. In order to achieve a concise synthesis, we chose to use allylic protective groups as permanent protective groups. We have also achieved α- and β-selective glycosylations for the respective linkages with high yields as the key steps.

AB - Efficient convergent chemical syntheses of digalactosyl diacylglycerols (DGDGs), which have both a galactose-galactose α(1→6)-linkage and a galactose-glycerol β-linkage along with a diacylglycerol containing various kinds of fatty acids, have been accomplished. In order to achieve a concise synthesis, we chose to use allylic protective groups as permanent protective groups. We have also achieved α- and β-selective glycosylations for the respective linkages with high yields as the key steps.

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Convergent Synthesis of Digalactosyl Diacylglycerols

Abstract

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