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A simple, stereoselective synthesis of ketomethylene dipeptide isosteres

โœ Scribed by Robert V. Hoffman; Junhua Tao

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
492 KB
Volume
53
Category
Article
ISSN
0040-4020

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โœฆ Synopsis

An exceedingly simple, general, and stereoselective method for the preparation of ketomethylene dipeptide isosteres (5-(carbobenzyloxyamino)-2-alkyl-~/-ketoesters) from Cbz-protected amino acids and scalemic 2-triflyloxy esters has been developed. The method is short (three steps), efficient, and highly diastereoselective and enantioselective.

๐Ÿ“œ SIMILAR VOLUMES

A stereocontrolled synthesis of monofluo
A stereocontrolled synthesis of monofluoro ketomethylene dipeptide isosteres
โœ Robert V. Hoffman; Junhua Tao ๐Ÿ“‚ Article ๐Ÿ“… 1998 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 242 KB

A simple, stel'eoc~ntrollod synthesis of monofluoro ketomethylene dipeptide isosteres has been developed. The method is short (6 sleps) and diastereoselective (85-95% de) and enantioselective (>95% ee).

Synthesis of hydroxyethylene and ketomet
Synthesis of hydroxyethylene and ketomethylene dipeptide isosteres
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A general stereo-directed synthesis of "ketomethylene" and "hydroxyethylene" dipeptide isosteres is reported. Peptides containing the amino acids, (2&%)-5-amino-4-oxo-2,8dimethyloctanoic acid (the "ketomethylene" analog of L-Leu-L-Ala), and (2&,5z)-5-amino-4-hydroxy-2,8-dimethyloctanoic acid (the "h