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Stereoselective synthesis of 2(S)-(1,1-dimethylethylsulfonylmethyl)-3-(1-naphthyl)-propionic acid, building block for protease inhibitors via asymmetric hydrogenation

✍ Scribed by Gerhard Beck; Heiner Jendralla; Bernhard Kammermeier

Book ID: 104203078
Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 599 KB
Volume: 50
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)85008-0

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✦ Synopsis

Title compound lb ('rity > 99%, 99.6% ee) is syrrthesized (IOOg scale) from commercial 3-bromo-pyruvic acid in six steps with on overall yield of 16% The sequence is operationally simple and devoid of chromatographic purijcations. Key step is the asymmetric hydmgenation of a substrate with sul/urjmctionality 2(s)-@err-Butylsulfonylmethyl)-3-aryl-propionic acids 1 are valuable N-terminal components in peptidomimetic protease inhibitors. BBP-OH la is used in activity -optimized inhibitors of human renin L2 , DSNP-OH lb is the best N-terminal in HIV-protease inhibitors of the phospbinic acid type 3 and in HBY 793 , one of the most potent HIV-protease inhibitors currently known .4 Rl R1 = Ph la "BBP-OH" R1 = 1-naphthyl lb "DSNP-OH"

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