246506-77-4

Basic information

• Product Name: 6-tert-butoxycarbonylamino-5-hydroxy-2-isopropyl-4-oxo-7-phenyl-3-azaheptanoic acid benzyl ester
• Synonyms: 6-tert-butoxycarbonylamino-5-hydroxy-2-isopropyl-4-oxo-7-phenyl-3-azaheptanoic acid benzyl ester
• CAS NO: 246506-77-4
• Molecular Weight: 484.593
• Mol File: 246506-77-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 6-tert-butoxycarbonylamino-5-hydroxy-2-isopropyl-4-oxo-7-phenyl-3-azaheptanoic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 6-tert-butoxycarbonylamino-5-hydroxy-2-isopropyl-4-oxo-7-phenyl-3-azaheptanoic acid benzyl ester(246506-77-4)
• EPA Substance Registry System: 6-tert-butoxycarbonylamino-5-hydroxy-2-isopropyl-4-oxo-7-phenyl-3-azaheptanoic acid benzyl ester(246506-77-4)

Safety Data

• Hazardous Substances Data: 246506-77-4(Hazardous Substances Data)

Upstream product

• 18942-49-9 Boc-D-Phe-OH 
• 246506-75-2 [1-benzyl-3-cyano-2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-carbamic acid tert-butyl ester 
• 172025-60-4 (2S,3R)-3-Azido-2-hydroxy-4-phenyl-butyric acid methyl ester 
• 612096-23-8 (2R,3S)-3-Bromo-2-hydroxy-4-phenyl-butyric acid methyl ester 
• 182699-39-4 (2S,3R)-methyl-2,3-epoxy-4-phenylbutanoic acid 
• 81926-51-4 N-(tert-butyloxycarbonyl)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 16652-76-9 L-valine benzyl ester p-toluenesulfonate salt 
• 62023-65-8 (2S,3R)-3-[(tert-butoxycarbonyl) amino]-2-hydroxy-4-phenyl-butanoic acid 
• 246506-76-3 6-tert-butoxycarbonylamino-2-isopropyl-4,5-dioxo-7-phenyl-3-azaheptanoic acid benzyl ester 

Downstream Products

• 612096-24-9 (S)-2-((2S,3R)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-3-methyl-butyric acid 
• 187402-73-9 2-[2-(3-amino-2-hydroxy-4-phenylbutyrylamino)-3-methylbutyrylamino]-3-phenylpropionic acid 
• 217480-76-7 (S)-2-[(S)-2-((2S,3R)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-3-methyl-butyrylamino]-3-phenyl-propionic acid 
• 217480-75-6 2-(6-tert-butoxycarbonylamino-5-hydroxy-2-isopropyl-4-oxo-7-phenyl-3-azaheptanoylamino)-3-phenylpropionic acid benzyl ester 

Relevant articles and documents

Application of acyl cyanophosphorane methodology to the synthesis of protease inhibitors: Poststatin, eurystatin, phebestin, probestin and bestatin

Full details are given for the syntheses of the protease inhibitors, poststatin and eurystatin by the acyl cyanophosphorane coupling procedure used for the formation of α-keto amides. We have also extended this methodology to the syntheses of the related α-hydroxy amide natural products, phebestin, probestin and bestatin. The key step in the latter synthetic sequences involved diastereomeric selectivity in the reduction of the α-keto precursor to the corresponding α-hydroxy amide by the use of zinc borohydride.

Synthesis of the peptidic α-hydroxy amides phebestin, probestin, and bestatin from α-keto amide precursors

Aminopeptidase inhibitors, phebestin, probestin and bestatin have been prepared by stereospecific reduction of α-keto amide precursors using zinc borohydride.