77327-06-1

Basic information

• Product Name: N-(L-Lac-N-Methyl-D-Leu-)cyclo[L-Thr*-[(3S,4R)-3-hydroxy-4-[(S)-1-methylpropyl]-γAbu-]-[(2S,4S)-4-hydroxy*-2,5-dimethyl-2-deamino-3-oxo-D-Nle-]-L-Leu-L-Pro-N,O-dimethyl-L-Tyr-]
• Synonyms: Didemnin C;N-(L-Lac-N-Methyl-D-Leu-)cyclo[L-Thr*-[(3S,4R)-3-hydroxy-4-[(S)-1-methylpropyl]-γAbu-]-[(2S,4S)-4-hydroxy*-2,5-dimethyl-2-deamino-3-oxo-D-Nle-]-L-Leu-L-Pro-N,O-dimethyl-L-Tyr-]
• CAS NO: 77327-06-1
• Molecular Formula: C₅₂H₈₂N₆O₁₄
• Molecular Weight: 1015.2393
• Mol File: 77327-06-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 1195.4°Cat760mmHg
• Flash Point: 676.8°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.559
• CAS DataBase Reference: N-(L-Lac-N-Methyl-D-Leu-)cyclo[L-Thr*-[(3S,4R)-3-hydroxy-4-[(S)-1-methylpropyl]-γAbu-]-[(2S,4S)-4-hydroxy*-2,5-dimethyl-2-deamino-3-oxo-D-Nle-]-L-Leu-L-Pro-N,O-dimethyl-L-Tyr-](CAS DataBase Reference)
• NIST Chemistry Reference: N-(L-Lac-N-Methyl-D-Leu-)cyclo[L-Thr*-[(3S,4R)-3-hydroxy-4-[(S)-1-methylpropyl]-γAbu-]-[(2S,4S)-4-hydroxy*-2,5-dimethyl-2-deamino-3-oxo-D-Nle-]-L-Leu-L-Pro-N,O-dimethyl-L-Tyr-](77327-06-1)
• EPA Substance Registry System: N-(L-Lac-N-Methyl-D-Leu-)cyclo[L-Thr*-[(3S,4R)-3-hydroxy-4-[(S)-1-methylpropyl]-γAbu-]-[(2S,4S)-4-hydroxy*-2,5-dimethyl-2-deamino-3-oxo-D-Nle-]-L-Leu-L-Pro-N,O-dimethyl-L-Tyr-](77327-06-1)

Safety Data

• Hazardous Substances Data: 77327-06-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C52H82N6O14/c1-15-30(8)42-40(60)26-41(61)72-45(29(6)7)44(62)31(9)46(63)53-36(23-27(2)3)50(67)58-22-16-17-37(58)51(68)57(13)39(25-34-18-20-35(70-14)21-19-34)52(69)71-33(11)43(48(65)54-42)55-47(64)38(24-28(4)5)56(12)49(66)32(10)59/h18-21,27-33,36-40,42-43,45,59-60H,15-17,22-26H2,1-14H3,(H,53,63)(H,54,65)(H,55,64)/t30-,31-,32?,33+,36-,37-,38+,39-,40-,42-,43-,45-/m0/s1

Upstream product

• 120286-09-1 Z-didemnin C 
• 110720-13-3 O-(Lac)-benzyldidemnin C 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 328-38-1 (R)-leucine 
• 65635-85-0 N-methyl-N-(benzyloxycarbonyl)-D-leucine 
• 110720-45-1 (3S,4R,5S)-4-(tert-butoxycarbonylamino)-3-(tert-butyldimethylsiloxy)-5-methylheptanoic acid 
• 110720-40-6 Z-D-MeLeu-Thr(OTMSe)-O-Me₂Tyr-Pro-Leu-Hip-Ist-Boc 
• 102123-88-6 L-leucine trimethylsilylethyl ester trifluoroacetate 
• 110720-19-9 (2S)-2-(benzyloxy)-3-methylbutanoyl chloride 
• 110720-22-4 Bzl-Hip-OH 
• 110720-20-2 ethyl O-benzyl-α-(α-hydroxyisovaleryl)propionate 
• 1027785-05-2 (3S,4R,5S)-ethyl 4-(tert-butoxycarbonylamino)-3-(tert-butyldimethylsiloxy)-5-methylheptanoate 
• 65903-62-0 N-benzyloxycarbonyl-L-leucine trimethylsilylethyl ester 
• 110720-28-0 H-Hip-Leu-OTMSe 

Relevant articles and documents

Total synthesis of the didemnins; IV. Synthesis of the peptolide ring and construction of the side chain

A total synthesis of didemnins A, B, and C (1-3) which enables these highly cytotoxic cyclopeptides to be prepared in decigram amounts is described. The β-keto acid unit (hydroxyisovaleryl)propionic acid derivative (Hip, 6) was prepared by acylation of dibenzyl methylmalonate and subsequent cleavage of the benzyl groups by the action of boron trichloride. The free β-keto acid 6 was activated by the DCC method and allowed to react with the leucine ester 7 to furnish the amide 8. Activation, deprotection, and ring closure of the linear peptide 19 by means of the pentafluorophenyl ester method in a two-phase system gave rise to the didemnin ring skeleton in 75% yield within a few minutes. The respective side chains were then attached to the didemnin ring easily and in high yields by activation of Z-(R)-N-methylleucine as its 3-cyano-2-pyridylthiol ester followed by reaction with Z-lactylproline chloride and Z-lactic acid chloride.

Total synthesis of the didemnins. 2. Synthesis of didemnin A, B, C and prolyldidemnin A

-