325687-69-2

Basic information

• Product Name: (3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-2-methyl-1-pentafluorophenyloxycarbonyl-propyl ester
• Synonyms: (3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-2-methyl-1-pentafluorophenyloxycarbonyl-propyl ester
• CAS NO: 325687-69-2
• Molecular Weight: 717.846
• Mol File: 325687-69-2.mol

Chemical Properties

• CAS DataBase Reference: (3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-2-methyl-1-pentafluorophenyloxycarbonyl-propyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-2-methyl-1-pentafluorophenyloxycarbonyl-propyl ester(325687-69-2)
• EPA Substance Registry System: (3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-2-methyl-1-pentafluorophenyloxycarbonyl-propyl ester(325687-69-2)

Safety Data

• Hazardous Substances Data: 325687-69-2(Hazardous Substances Data)

Upstream product

• 60129-85-3 Perfluorophenyl trifluoromethanesulfonate 
• 325687-68-1 (3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-1-carboxy-2-methyl-propyl ester 
• 1685-33-2 N-[(benzyloxy)carbonyl]-D-valine 
• 147778-58-3 (4R)-4-benzyloxycarbonylamino-3-oxo-hexanoic acid methyl ester 
• 178113-56-9 L-2-hydroxy-3-methylbutanoic acid allyl ester 
• 325687-64-7 (3S,4R)-4-benzyloxycarbonylamino-3-hydroxyhexanoic acid methyl ester 
• 325687-65-8 (3S,4R)-4-benzyloxycarbonylamino-3-(triisopropylsilanyloxy)hexanoic acid methyl ester 
• 325687-66-9 (3S,4R)-4-benzyloxycarbonylamino-3-(triisopropylsilanyloxy)heptanoic acid 
• 325687-67-0 (3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester 
• 640-68-6 D-Val-OH 
• 72-18-4 L-valine 
• 17407-55-5 (S)-2-Hydroxy-3-methylbutanoic acid 
• 501-53-1 benzyl chloroformate 
• 325687-63-6 N-Z-D-valine pentafluorophenyl ester 

Downstream Products

• 258339-38-7 (-)-tamandarin B 
• 1053247-83-8 4-amino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid 1-[1-(2-{[1-(2-tert-butoxycarbonylamino-2-carboxy-1-methyl-ethoxycarbonyl)-2-(4-methoxy-phenyl)-ethyl]-methyl-carbamoyl}-pyrrolidine-1-carbonyl)-3-methyl-butylcarbamoyl]-2-methyl-propyl ester 
• 325687-71-6 [5-isobutyl-8,13-diisopropyl-20-(4-methoxy-benzyl)-17,21-dimethyl-4,7,10,15,19,22-hexaoxo-12-triisopropylsilanyloxy-eicosahydro-9,18-dioxa-3a,6,14,21-tetraaza-cyclopentacycloheneicosen-16-yl]-carbamic acid tert-butyl ester 
• 325687-70-5 C₆₆H₁₀₉N₅O₁₆Si₂ 

Relevant articles and documents

Total syntheses and biological investigations of tamandarins A and B and tamandarin A analog

Tamandarins A (1) and B (2), two natural products similar in structure to didemnin B (3), were recently isolated from a Brazilian marine ascidian of the family Didemnidae. The cytotoxicity of 1 was reported to be somewhat more potent in vitro than that of 3 against various human cancer cell lines. The present account describes the first total syntheses of 1 and 2, and the syntheses of tamandarin A side chain analogues. The cytotoxicity data for these compounds show that the side chain modifications exhibit a parallel effect for both didemnins and tamandarins. This observation supports tamandarins' role as didemnins' mimic.

Total synthesis of (-)-tamandarin B

The synthesis of tamandarin B is described. Key steps in the synthesis of the macrocycle component include a diastereoselective ketone reduction, linear precursor formation via an activated pentafluorophenyl ester, and HATU-promoted cyclization. Side-chain coupling was achieved in excellent yield with the newly developed coupling reagent DEPBT. (C) 2000 Published by Elsevier Science Ltd.