Stereoselective synthesis of α-linked 2-deoxy glycosides enabled by visible-light-mediated reductive deiodination.
2-Deoxy sugars and their derivatives occur abundantly in many pharmaceutically important natural products. However, the construction of specific 2-deoxy-glycosidic bonds remains as a challenge. Herein, we report an efficient way to prepare 2-deoxy-α-glycosides by glycosylation of 2-iodo-glycosyl acetate and subsequent visible-light-mediated tin-free reductive deiodination. We have successfully applied the postglycosylational-deiodination strategy in the synthesis of more than 30 mono-, di-, tri-, tetra- and pentadeoxysaccharides with excellent stereoselectivity and efficiency. This method has also been applied to the synthesis of a 2-deoxy-tetrasaccharide containing four α-linkages.
Tongji School of Pharmacy, Huazhong University of Science and Technology, 13 Hangkong Road, Wuhan, Hubei, 430030 (P. R. China).
Hao
H
Wang
Jinyi
J
Tao
Xinpei
X
Cai
Wei
W
Chen
Yueqi
Y
Zhao
Yang
Y
Xu
Wang
W
Yao
Jing
J
Zeng
Qian
Q
Wan
D003837:Deoxy Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D054879:Halogenation; D007455:Iodine / Q000737:chemistry*; D008027:Light; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D003837:Deoxy Sugars; D009844:Oligosaccharides; D007455:Iodine
deiodination; glycosides; glycosylation; photocatalysis; radical reaction