SN2-Type Glycosylation with Unprotected Pyranoses
| Autor: | Hiromitsu Shibayama, Norihiro Tokitoh, Tomoyuki Yoshimura, Yusuke Fujimori, Masaru Nagaishi, Hironori Takeuchi, Takahiro Sasamori, Takeo Kawabata, Yoshihiro Ueda, Takumi Furuta |
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| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
animal structures Glycosylation Stereochemistry Carboxylic acid Total synthesis macromolecular substances carbohydrates (lipids) chemistry.chemical_compound SN1 reaction chemistry Stereoselectivity Glycosyl Mitsunobu reaction lipids (amino acids peptides and proteins) Benzoic acid |
| DOI: | 10.26434/chemrxiv.11276384 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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