73397-20-3

Usage

Chemical Properties

White powder

Upstream product

• 73397-27-0 (2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-5-methylhexanoic acid 
• 111060-65-2 (S)-2-(dibenzylamino)-4-methylpentanal 
• 118970-39-1 (2S,3S)-3-(dibenzylamino)-2-hydroxy-5-methylhexanenitrile 
• 81322-83-0 (S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-5-methyl-2-trimethylsilanyloxy-hexanenitrile 
• 112803-68-6 methyl DL-threo-3-amino-2-hydroxy-5-methylhexanoate 
• 143-33-9 sodium cyanide 
• 87024-12-2 (S)-1-(2'-benzyloxycarbonylamino-4'-methylpentanoyl)-3,5-dimethylpyrazole 
• 73397-22-5 Cbz-D-Leu-OMe 
• 70853-26-8 (R)-4-methyl-1-oxopentane-2-benzylcarbamate 
• 63219-62-5 [(S)-1-((S)-Cyano-hydroxy-methyl)-3-methyl-butyl]-carbamic acid benzyl ester 
• 590-86-3 isovaleraldehyde 
• 75513-59-6 methyl threo-3-hydroxy-2-tosyloxy-5-methylhexanoate 
• 75410-06-9 methyl cis-2,3-epoxy-5-methylhexanoate 
• 75513-58-5 methyl threo-2,3-dihydroxy-5-methylhexanoate 

Downstream Products

• 73397-25-8 (2S,3R)-3-tert-Butoxycarbonylamino-2-hydroxy-5-methyl-hexanoic acid 
• 318464-20-9 (2R,3S)-3-amino-2-hydroxy-5-methylhexanoic acid 
• 73397-27-0 (2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-5-methylhexanoic acid 
• 73397-25-8 (2RS,3R)-3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoic Acid 
• 73397-34-9 (2S,3R)-<3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoyl>-L-valyl-L-valyl-aspartic Acid Dibenzyl Ester 
• 73465-22-2 (2R,3R)-<3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoyl>-L-valyl-L-valyl-aspartic Acid Dibenzyl Ester 
• 73397-25-8 (2S,3R)-3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoic Acid 
• 73397-26-9 (2R,3R)-3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoic Acid 
• 73465-23-3 (2R,3R)-(3-Amino-2-hydroxy-5-methylhexanoyl)-L-valyl-L-valyl-L-aspartic Acid 
• 67655-94-1 amastatin 
• 73397-28-1 (2R,3S)-3-(N-boc)amino-2-hydroxy-5-methylhexanoic acid 

Relevant academic research and scientific papers

TAXANE DERIVATIVES AND PROCESSES FOR THE PREPARATION THEREOF

The invention discloses an oxazolidine intermediate for the synthesis of 14- beta -hydroxy-1,14-carbonate-baccatines bearing a 13-isoserine substituent, and a process for the preparation thereof.

Stereoselective cyanation of chiral α-amino aldehydes by reaction with Nagata's reagent: A route to enantiopure β-amino-α-hydroxy acids

Chiral α-dibenzylamino aldehydes react with diethylaluminum cyanide leading to anti-β-dibenzylamino-α-hydroxycyanides as the major diastereoisomers in good yields and diastereomeric excesses. Hydrolysis of the nitrile derivatives allows the synthesis of enantiopure β-amino-α-hydroxy acids.

Synthesis of (2S,3R)-3-Amino-2-hydroxy-5-methylhexanoic Acid: Bridging Effect of KF

Natural (2S,3R)-3-amino-2-hydroxy-5-methylhexanoic acid is synthesized in 53-55percent yield (referred to (-)-8-phenylmenthol used as chiral auxiliary) by condensation of 1-nitro-3-methylbutane on (-)-8-phenylmenthol glyoxylate hydrate using KF as a mild base.With a large excess of KF in THF it has been possible to increase the diastereoselectivity of the nitro aldol condensation (up to I/II/III/IV = 77/13/10/0).

Renin Inhibitors. Substitution of the Leucyl Residues of Leu-Leu-Val-Phe-OCH3 with 3-Amino-2-hydroxy-5-methylhexanoic Acid

The 2S,3S and 2R,3S diastereoisomers of the hydroxy amino acid 3-amino-2-hydroxy-5-methylhexanoic acid (AHMHA) were synthesized and substituted for the leucyl residues of Leu-Leu-Val-Phe-OCH3 to yield the following analogues: AHMHA-Leu-Val-Phe-OCH3, AHMHA

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.