Synlett 2018; 29(20): 2701-2706
DOI: 10.1055/s-0037-1611311
letter
© Georg Thieme Verlag Stuttgart · New York

Effect of Anomeric Configuration on Stereocontrolled α-Glycosylation of l-Fucose

Lihao Wang ◊
a  Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China   Email: caic@ouc.edu.cn
c  Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Fei Fan ◊
a  Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China   Email: caic@ouc.edu.cn
c  Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Haotian Wu
a  Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China   Email: caic@ouc.edu.cn
c  Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Lei Gao
a  Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China   Email: caic@ouc.edu.cn
c  Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Ping Zhang
a  Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China   Email: caic@ouc.edu.cn
c  Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Tiantian Sun
a  Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China   Email: caic@ouc.edu.cn
c  Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Chendong Yang
a  Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China   Email: caic@ouc.edu.cn
c  Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Guangli Yu
a  Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China   Email: caic@ouc.edu.cn
b  Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266003, P. R. of China
c  Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Chao Cai*
a  Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China   Email: caic@ouc.edu.cn
b  Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266003, P. R. of China
c  Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
› Author Affiliations
This work was financially supported by Fundamental Research Funds for the Central Universities (201762002), Natural Science Foundation of Shandong Province (ZR2016BB02), Primary Research and Development Plan of Shandong Province (2017GSF221002), Basic Research Funds for Application of Qingdao (17-1-1-63-jch), National Natural Science Foundation of China and NSFC-Shandong Joint Fund for Marine Science Research Centers (21602212, 31670811, U1606403), Major Science and Technology Projects in Shandong Province (2015ZDJS04002), China Postdoctoral Science Foundation (2016M590664, 2017T100519), Shandong Provincial Key Laboratory of Glycoscience Industry Alliance, Taishan Scholar Project Special Funds, as well as Qingdao Scientific and Technological Innovation Center for Marine Biomedicine Development Grant.
Further Information

Publication History

Received: 25 August 2018

Accepted after revision: 08 October 2018

Publication Date:
23 November 2018 (online)


These authors contributed equally to this work

Abstract

In this letter, we report an approach to the stereoselective α-glycosylation of l-fucose that is exemplified by effect of anomeric configuration. The neighboring group participation is not compatible with α-glycosylation of l-fucose, therefore the remote participation by 4-O-Bz was employed to control the formation of 1,2-cis-glycosidic bond. Furthermore, we found the anomeric configuration of fucose donor is crucial to stereoselectivity of the glycosylated products. The α/β-mixed products were generated by using β-anomeric donor while the glycosyl donor in α configuration yielded products in high α-selectivity possibly due to the distinct pathway to forming the key intermediates. This phenomenon supplies the basis for the synthesis of complicated natural carbohydrates containing fucose α-glycoside, such as fucoidans, fucosylated N-glycans, and fucosylated chondroitin sulfates, etc.

Supporting Information

 
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