Journal
ORGANIC LETTERS
Volume 22, Issue 12, Pages 4754-4759Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c01549
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Funding
- Naito Foundation
- JSPS [JP13J03416]
- [JP26221301]
- [JP15K18827]
- [JP23105008]
- [JP16H01148]
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An S(N)2 mechanism was proposed for highly stereoselective glycosylation of benzoic acid with unprotected alpha-D-oglucose under Mitsunobu conditions in dioxane, while an S(N)1 mechanism was indicated for nonstereoselective glycosylation in DMF. The S(N)2-type stereoselective Mitsunobu glycosylation is generally applicable to various unprotected pyranoses as glycosyl donors in combination with a wide range of acidic glycosyl acceptors such as carboxylic acids, phenols, and imides, retaining its high stereoselectivity (33 examples). Glycosylation of a carboxylic acid with unprotected alpha-D-mannose proceeded also in an S(N)2 manner to directly afford a usually less accessible 1,2-cis-mannoside. One- or two-step total syntheses of five simple natural glycosides were performed using the glycosylation strategy presented here using unprotected alpha-D-glucose.
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