TY - JOUR
T1 - Recent development of stereoselective glycosylation reactions
AU - Manabe, Shino
N1 - Funding Information:
S. M. expressed my heartfelt thanks to my collaborators, especially Dr. Kazuyuki Ishii (RIKEN). S. M. would like to thank to Dr. Yukishige Ito (RIKEN) to discussions. These results were supported by Grant-in-Aid for Scientific Research (B) (Grant No. 19H03357) from the Japan Society for Promotion of Science, Yamada Science Foundation, Takeda Science Foundation, and A-STEP from JST.
PY - 2021
Y1 - 2021
N2 - Carbohydrates are the most abundant class among biological molecules. Advances in glycobiology have revealed the vital roles played by glycosides and glycoconjugates in biological events. In this context, access to homogenous oligosaccharides and glycoconjugates is critical for various biological investigations. Glycosylation is the cornerstone of glycoside synthesis, and during glycosylation, the control of stereoselectivity at the anomeric position is highly important. In this review, recent progresses in 1,2-cis-glycosylation reactions are summarized, with a focus on the influence of the protecting groups on the conformations of the glycosyl donors, role of reaction mixture additives, and synthetic utility of endocyclic cleavage of glycoside. Development of robust glycosylation reaction will contribute to biologically active oligosaccharide synthesis.
AB - Carbohydrates are the most abundant class among biological molecules. Advances in glycobiology have revealed the vital roles played by glycosides and glycoconjugates in biological events. In this context, access to homogenous oligosaccharides and glycoconjugates is critical for various biological investigations. Glycosylation is the cornerstone of glycoside synthesis, and during glycosylation, the control of stereoselectivity at the anomeric position is highly important. In this review, recent progresses in 1,2-cis-glycosylation reactions are summarized, with a focus on the influence of the protecting groups on the conformations of the glycosyl donors, role of reaction mixture additives, and synthetic utility of endocyclic cleavage of glycoside. Development of robust glycosylation reaction will contribute to biologically active oligosaccharide synthesis.
UR - http://www.scopus.com/inward/record.url?scp=85099196551&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85099196551&partnerID=8YFLogxK
U2 - 10.3987/REV-20-933
DO - 10.3987/REV-20-933
M3 - Article
AN - SCOPUS:85099196551
VL - 102
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
IS - 2
ER -