17543-45-2

Basic information

• Product Name: 1,2-Pyrrolidinedicarboxylic acid, 2-(pentafluorophenyl) 1-(phenylmethyl) ester, (2S)-
• CAS NO: 17543-45-2
• Molecular Formula: C19H14F5NO4
• Molecular Weight: 415.316
• Mol File: 17543-45-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1,2-Pyrrolidinedicarboxylic acid, 2-(pentafluorophenyl) 1-(phenylmethyl) ester, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Pyrrolidinedicarboxylic acid, 2-(pentafluorophenyl) 1-(phenylmethyl) ester, (2S)-(17543-45-2)
• EPA Substance Registry System: 1,2-Pyrrolidinedicarboxylic acid, 2-(pentafluorophenyl) 1-(phenylmethyl) ester, (2S)-(17543-45-2)

Safety Data

• Hazardous Substances Data: 17543-45-2(Hazardous Substances Data)

Upstream product

• 771-61-9 2,3,4,5,6-pentafluorophenol 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 

Downstream Products

• 194933-36-3 (S)-2-((S)-2-Methyl-5-oxo-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 287401-29-0 1-oxo-3-phenyl-2-oxa-5-aza-spiro[3.4]octane-5-carboxylic acid benzyl ester 
• 149525-70-2 Z-Asp(OBzl)-Pro-Arg-OH 
• 2418-74-8 L-prolyl-L-arginine 
• 60889-67-0 N-benzyloxycarbonyl-L-prolyl-L-arginine 
• 287401-28-9 1,1-dimethyl-3-oxo-2-oxa-5-aza-spiro[3.4]octane-5-carboxylic acid benzyl ester 
• 210777-22-3 (S)-2-((R)-4-[(S)-2-tert-Butoxycarbonylamino-3-(4-tert-butoxycarbonyloxy-phenyl)-propionylamino]-4-{[((S)-1-carboxy-2-phenyl-ethylcarbamoyl)-methyl]-carbamoyl}-butylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl 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.

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