TY - JOUR
T1 - Diboron-Catalyzed Regio- And 1,2- cis-α-Stereoselective Glycosylation of trans-1,2-Diols
AU - Tomita, Shunpei
AU - Tanaka, Masamichi
AU - Inoue, Michitaka
AU - Inaba, Kazuki
AU - Takahashi, Daisuke
AU - Toshima, Kazunobu
N1 - Funding Information:
This research was supported in part by the JSPS KAKENHI Grant Number JP19H02724 in Scientific Research (B).
Publisher Copyright:
© 2020 American Chemical Society.
PY - 2020/12/18
Y1 - 2020/12/18
N2 - Regio- and 1,2-cis-α-stereoselective glycosylations were investigated using 1,2-anhydroglucose donors and trans-1,2-diol sugar acceptors in the presence of a diboron catalyst. The reactions proceeded smoothly to provide the corresponding 1,2-cis-α-glycosides with consistently very high stereoselectivity and were regioselectivity controlled by the protecting groups of the acceptor. The present glycosylation method was applied successfully to the efficient synthesis of α-1,3-glucan pentasaccharide.
AB - Regio- and 1,2-cis-α-stereoselective glycosylations were investigated using 1,2-anhydroglucose donors and trans-1,2-diol sugar acceptors in the presence of a diboron catalyst. The reactions proceeded smoothly to provide the corresponding 1,2-cis-α-glycosides with consistently very high stereoselectivity and were regioselectivity controlled by the protecting groups of the acceptor. The present glycosylation method was applied successfully to the efficient synthesis of α-1,3-glucan pentasaccharide.
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U2 - 10.1021/acs.joc.0c02093
DO - 10.1021/acs.joc.0c02093
M3 - Article
AN - SCOPUS:85096194934
SN - 0022-3263
VL - 85
SP - 16254
EP - 16262
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 24
ER -