194933-46-5

Basic information

• Product Name: L-Valine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-L-threonyl-N-methyl-, methyl ester
• CAS NO: 194933-46-5
• Molecular Formula: C23H36N2O6
• Molecular Weight: 436.549
• Mol File: 194933-46-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: L-Valine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-L-threonyl-N-methyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Valine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-L-threonyl-N-methyl-, methyl ester(194933-46-5)
• EPA Substance Registry System: L-Valine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-L-threonyl-N-methyl-, methyl ester(194933-46-5)

Safety Data

• Hazardous Substances Data: 194933-46-5(Hazardous Substances Data)

Upstream product

• 24164-06-5 methyl (2S)-2-[(tert-butoxycarbonyl)(methyl)amino]-3-methylbutanoate 
• 45170-31-8 Boc-N-Me-Val-OH 
• 13734-41-3 t-Boc-L-valine 
• 15260-10-3 N-Boc-O-benzyl-L-threonine 
• 3339-44-4 methyl N-methyl-L-valinate hydrochloride 

Downstream Products

• 194933-50-1 microcolin C 
• 194933-48-7 (S)-2-[((2S,3R)-3-Benzyloxy-2-{(S)-2-[((2R,4R)-2,4-dimethyl-octanoyl)-methyl-amino]-4-methyl-pentanoylamino}-butyryl)-methyl-amino]-3-methyl-butyric acid methyl ester 
• 194933-49-8 (S)-2-[((2S,3R)-3-Benzyloxy-2-{(S)-2-[((2R,4R)-2,4-dimethyl-octanoyl)-methyl-amino]-4-methyl-pentanoylamino}-butyryl)-methyl-amino]-3-methyl-butyric acid 
• 194933-47-6 (S)-2-({(2S,3R)-3-Benzyloxy-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-butyryl}-methyl-amino)-3-methyl-butyric acid methyl ester 

Relevant articles and documents

Synthesis of Microcolin B, a Potent New Immunosuppressant Using an Efficient Mixed Imide Formation Reaction

Microcolin B, a potent new immunosuppressant isolated from blue-green alga Lyngbya majuscula off the Venezuelan coast, has been made using a methyl-directed asymmetric hydrogenation reaction with rhodium on alumina catalyst on lactone 4 for the synthesis of the key (R,R)-2,4-dimethyl-octanoic acid fragment 1. A new, direct mixed imide formation reaction was also developed for the production of the unusual prolylpyrrolen-2-one 2 portion of microcolin. The pentafluorophenyl ester of CBZ-proline 5 was reacted with the lithium imidate of lactam 6, providing the mixed imide in 80% yield. Coupling of acid 1 with the N-terminus of the tripeptide, followed by coupling with pyrrolylproline 2, gave microcolin B. The new mixed-imide forming reaction was also applied to a formal total synthesis of microcolin A. The pentafluorophenyl ester of TBS-protected cis-hydroxyproline was coupled with lactam 6, and the resultant imide was converted to the key pyrrolylproline made previously for microcolin A.