73397-34-9

Basic information

• Product Name: (2S,3R)-<3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoyl>-L-valyl-L-valyl-aspartic Acid Dibenzyl Ester
• Synonyms: (2S,3R)-<3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoyl>-L-valyl-L-valyl-aspartic Acid Dibenzyl Ester
• CAS NO: 73397-34-9
• Molecular Weight: 754.921
• Mol File: 73397-34-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3R)-<3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoyl>-L-valyl-L-valyl-aspartic Acid Dibenzyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-<3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoyl>-L-valyl-L-valyl-aspartic Acid Dibenzyl Ester(73397-34-9)
• EPA Substance Registry System: (2S,3R)-<3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoyl>-L-valyl-L-valyl-aspartic Acid Dibenzyl Ester(73397-34-9)

Safety Data

• Hazardous Substances Data: 73397-34-9(Hazardous Substances Data)

Upstream product

• 73397-22-5 Cbz-D-Leu-OMe 
• 2886-33-1 dibenzyl L-aspartate toluene-4-sulphonate 
• 70853-26-8 (R)-4-methyl-1-oxopentane-2-benzylcarbamate 
• 70853-22-4 <(tert-Butyloxy)carbonyl>-L-valyl-L-valyl-L-aspartic Acid Dibenzyl Ester 
• 73397-25-8 (2RS,3R)-3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoic Acid 
• 63219-62-5 [(S)-1-((S)-Cyano-hydroxy-methyl)-3-methyl-butyl]-carbamic acid benzyl ester 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 62023-30-7 (2RS,3R)-3-Amino-2-hydroxy-5-methylhexanoic Acid 
• 13734-41-3 t-Boc-L-valine 

Downstream Products

• 67655-94-1 amastatin 

Relevant articles and documents

Synthesis of (2S,3R)-3-Amino-2-hydroxy-5-methylhexanoic Acid Derivatives. Application to the Synthesis of Amastatin, an Inhibitor of Aminopeptidases

Methods are reported for the synthesis of optically pure derivatives of (2S,3R)-3-amino-2-hydroxy-5-methylhexanoic acid. -D-leucine methyl ester was reduced in 95percent yield with diisobutylaluminum hydride to the aldehyde which was converted via the cyanohydrin to (2RS,3R)-3-amino-2-hydroxy-5-methylhexanoic acid (AHMHA).The mixture of diastereomers was converted to the corresponding Boc-AHMHA methyl ester derivatives and separated by chromatography over silica gel.The optical purity of the diastereomers at C-3 was established by converting each to diastereomeric Boc-AHMHA-Leu-OMe and separating these dipeptides by chromatography.Pure (2S,3R)-Boc-AHMHA was coupled with valyl-valyl-aspartic acid dibenzyl ester by using dicyclohexylcarbodiimide/ 1-hydroxybenzotriazole in 63percent yield.The Boc group was removed by using trifluoroacetid acid, and the benzyl groups were removed by hydrogenolysis.The product, (2S,3R)-AHMHA-L-Val-L-Val-L-Asp, amastatin, was found to be identical with the natural product.