Thermodynamically Controlled Regioselective Glycosylation of Fully Unprotected Sugars through Bis(boronate) Intermediates
Thermodynamically Controlled Regioselective Glycosylation of Fully Unprotected Sugars through Bis(boronate) Intermediates
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DOI：
10.1002/ejoc.201402255
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发表时间：
2014-06-01
影响因子：
2.8
通讯作者：
Nishino, Takashi
中科院分区：
文献类型：
--
作者：
Kaji, Eisuke;Yamamoto, Daisuke;Nishino, Takashi
Fully unprotected D-glucose, D-mannose, and D-fructose were regioselectively glycosylated with several phenylthioglycosides to afford glycosyl-beta(1 -> 6)-alpha/beta-D-glucopyranose, glycosyl-beta(1 -> 1)-alpha-D-mannofuranoside, and glycosyl-beta(1 -> 1)-alpha-D-fructopyranose in good yields. The regioselectivity might have arisen from a thermodynamically controlled bis(phenylboronate) intermediate, which leaves only one free hydroxy group to be glycosylated in complete regioselectivity.
