TY - JOUR
T1 - Boronic-acid-catalyzed regioselective and stereoselective glycosylations via sni-type mechanism
AU - Takahashi, Daisuke
N1 - Funding Information:
The work presented here was conducted in the Molecular Life Chemistry Lab at Keio University. The author would like to express his sincere appreciation to Prof. Kazunobu Toshima, all past and present lab members, and all the co-workers who have worked on this project. This work was supported in part by the MEXT-supported Program for the Strategic Research Foundation at Private Universities, 2012–2016 (No. S1201020), Kaneka Corporation Award in Synthetic Organic Chemistry, Japan, JSPS KAKENHI Grant Numbers JP16K05781 and JP16H01161 in Middle Molecular Strategy, a SUNBOR Grant from the Suntory Foundation for Life Sciences, and the Sasagawa Scientific Research Grant from the Japan Science Society.
Publisher Copyright:
© 2019 FCCA (Forum: Carbohydrates Coming of Age).
PY - 2019/7
Y1 - 2019/7
N2 - 1,2-cis-Glycosides are frequently found in various biologically active natural products. However, the stereoselective synthesis of these glycosides is still difficult due to the lack of neighboring group participation. Therefore, the development of efficient synthetic methods has been required. In this context, we have reported novel regio-and 1,2-cis-α-stereoselective glycosylations using 1,2-anhydroglycosyl donors and diol acceptor-derived boronic ester catalysts without additives under mild conditions. In addition, development of 1,2-cis-stereoselective glycosylations using mono-ol acceptor-derived borinic esters and their application to the total synthesis of natural glycolipids were also reported. In this mini-review, further extended studies on boronic-acid-catalyzed regio-and stereoselective glycosylations are introduced.
AB - 1,2-cis-Glycosides are frequently found in various biologically active natural products. However, the stereoselective synthesis of these glycosides is still difficult due to the lack of neighboring group participation. Therefore, the development of efficient synthetic methods has been required. In this context, we have reported novel regio-and 1,2-cis-α-stereoselective glycosylations using 1,2-anhydroglycosyl donors and diol acceptor-derived boronic ester catalysts without additives under mild conditions. In addition, development of 1,2-cis-stereoselective glycosylations using mono-ol acceptor-derived borinic esters and their application to the total synthesis of natural glycolipids were also reported. In this mini-review, further extended studies on boronic-acid-catalyzed regio-and stereoselective glycosylations are introduced.
KW - Borinic acid
KW - Boronic acid
KW - Glycosylation
KW - Organoboron compound
KW - Regioselective
KW - Si-type mechanism
KW - Stereoselective
KW - Unprotected glycoside
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U2 - 10.4052/tigg.1944.2SE
DO - 10.4052/tigg.1944.2SE
M3 - Article
AN - SCOPUS:85071032484
SN - 0915-7352
VL - 31
SP - SE93-SE94
JO - Trends in Glycoscience and Glycotechnology
JF - Trends in Glycoscience and Glycotechnology
IS - 181
ER -