A practical diastereoselective synthesis of (−)‐bestatin | Zendy

Shang Suisheng | Zendy; Willems Andreas V. | Zendy; Chauhan Satendra S. | Zendy

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A practical diastereoselective synthesis of (−)‐bestatin

Author(s) -

Shang Suisheng,

Willems Andreas V.,

Chauhan Satendra S.

Publication year - 2018

Publication title -

journal of peptide science

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.475

H-Index - 66

eISSN - 1099-1387

pISSN - 1075-2617

DOI - 10.1002/psc.3067

Subject(s) - oxazolidine , chemistry , diastereomer , sodium hydride , nitromethane , column chromatography , yield (engineering) , ether , organic chemistry , metallurgy , materials science

Diastereoselective addition of nitromethane to Boc‐ D ‐Phe‐H in the presence of sodium hydride in diethyl ether/hexane containing 15‐crown‐5 and subsequent N,O ‐protection with 2,2‐dimethoxypropane gave trans ‐oxazolidine in a diastereomeric ratio of >16:1. The oxazolidine was easily separated by column chromatography, which after Nef reaction was coupled to H‐Leu‐O t Bu. The 8‐step synthesis afforded (−)‐bestatin in an overall yield of 24.7% after deprotection and ion exchange.

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