118878-63-0

Basic information

• Product Name: Z-Thr(Boc-Pro-MeTyr(Me))-Ist-Hip-Leu-OTCE
• CAS NO: 118878-63-0
• Molecular Weight: 1199.66
• Mol File: 118878-63-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Z-Thr(Boc-Pro-MeTyr(Me))-Ist-Hip-Leu-OTCE(CAS DataBase Reference)
• NIST Chemistry Reference: Z-Thr(Boc-Pro-MeTyr(Me))-Ist-Hip-Leu-OTCE(118878-63-0)
• EPA Substance Registry System: Z-Thr(Boc-Pro-MeTyr(Me))-Ist-Hip-Leu-OTCE(118878-63-0)

Safety Data

• Hazardous Substances Data: 118878-63-0(Hazardous Substances Data)

Upstream product

• 135103-23-0 Z-Thr(H-MeTyr(Me))-OPE 
• 118878-60-7 (3S,4R)-4-Amino-3-hydroxy-5-methyl-heptanoic acid (S)-1-isopropyl-3-[(S)-3-methyl-1-(2,2,2-trichloro-ethoxycarbonyl)-butylcarbamoyl]-2-oxo-butyl ester 
• 135103-24-1 Z-Thr(Boc-Pro-MeTyr(Me))-OPE 
• 135103-28-5 Z-Thr(H-MeTyr(Me))-OPE hydrochloride 
• 135103-22-9 Z-Thr(Boc-MeTyr(Me))-OPE 
• 135103-21-8 Boc-(3S,4R,5S)-Ist(TBDMS)-(2RS,4S)-Hip-Leu-OTCE 
• 135103-19-4 dibenzyl (S)-⁽³⁾-chloroacetoxy-1,4-dimethyl-2-oxopentane-1,1-dicarboxylate 
• 40126-80-5 trichloroethyl (S)-leucinate hydrochloride 
• 135103-26-3 Boc-(3S,4R,5S)-Ist-(TBDMS)-OTBDMS 
• 92463-56-4 N-benzyloxycarbonyl-(S)-threonine phenacyl ester 
• 118878-59-4 H-(2RS,4S)-Hip-Leu-OTCE 
• 110720-45-1 N-Boc-O-tert-butyldimethylsilyl-(3S,4R,5S)-isostatine 
• 118171-78-1 Boc-(3S,4R,5S)-Ist-OH 
• 73584-84-6 (S)-2-(tert-butoxycarbonyl(methyl)amino)-3-(4-methoxyphenyl)propanoic acid 

Downstream Products

• 77327-04-9 Didemnin A 
• 77327-06-1 didemnin C 
• 130008-93-4 cyclo--5-methylheptanoyl>oxy-3-oxo-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-N,O-dimethyl-L-tyrosyl>-L-threonyl> hydrochloride 
• 110720-12-2 N-Z-didemnin A 
• 114607-50-0 didemnin B 
• 118919-23-6 C₅₀H₇₁N₅O₁₃ 
• 118878-64-1 C₅₀H₇₁N₅O₁₃ 
• 120286-08-0 Z-didemnin B 
• 148914-68-5 C₆₁H₈₀F₅N₅O₁₆ 
• 120286-09-1 Z-didemnin C 
• 148914-68-5 C₆₁H₈₀F₅N₅O₁₆ 
• 148914-67-4 C₅₅H₈₁N₅O₁₆ 
• 148914-67-4 C₅₅H₈₁N₅O₁₆ 

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.