SN2-Type glycosylation with unprotected pyranoses

Hironori Takeuchi, Yusuke Fujimori, Hiromitsu Shibayama, Masaru Nagaishi, Yoshihiro Ueda, Tomoyuki Yoshimura, Takahiro Sasamori, Norihiro Tokitoh, Takumi Furuta, Takeo Kawabata

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Dec 03, 2019
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Received Date: 18th November 19

An SN2 mechanism was proposed for highly stereoselective glycosylation of benzoic acid with unprotected α-D-glucose under Mitsunobu conditions in dioxane, while an SN1 mechanism seems to be responsible for non-stereoselective glycosylation in DMF. The SN2-type glycosylation can be applicable to various unprotected pyranoses as glycosyl donors and a wide range of carboxylic acids, phenols, and imides as glycosyl acceptors, retaining its high stereoselectivity (34 examples). Glycosylation of a carboxylic acid with unprotected α-D-mannose proceeded also in an SN2 manner to directly afford a usually less accessible 1,2-cis-mannoside. An extremely short-step total synthesis of a middle molecule (1874 Da) natural glycoside with antitumor activity, coriariin A, was achieved via a double SN2 glycosylation strategy with two molecules of unprotected α-D-glucose.

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This is an abstract of a preprint hosted on an independent third party site. It has not been peer reviewed but is currently under consideration at Nature Communications.

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