A Glycal Approach to the Synthesis of Steviamine Analogues | Zendy

Santhanam Venkatesan | Zendy; Ramesh Namakkal G. | Zendy

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A Glycal Approach to the Synthesis of Steviamine Analogues

Author(s) -

Santhanam Venkatesan,

Ramesh Namakkal G.

Publication year - 2014

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201402943

Subject(s) - chemistry , glycal , glucal , pyrrolidine , sulfone , glycoside hydrolase , stereochemistry , ethyl acetoacetate , stereoselectivity , organic chemistry , enzyme , catalysis

The synthesis of two new stereoisomers of steviamine, namely 1,8a‐di‐ epi ‐(+)‐steviamine and 2,3‐di‐ epi ‐(–)‐steviamine, is reported, starting from tri‐ O ‐benzyl‐ D ‐glucal. The key step in the synthesis was a modified Julia olefination of a 2‐formyl‐polyhydroxy‐pyrrolidine with a sulfone derived from ethyl acetoacetate. Glycosidase‐inhibition studies revealed that 2,3‐di‐ epi ‐(–)‐steviamine is a selective inhibitor of α‐galactosidase.

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