159360-04-0

Basic information

• Product Name: (4R,5S)-4-benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid methyl ester
• Synonyms: (4R,5S)-4-benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid methyl ester
• CAS NO: 159360-04-0
• Molecular Weight: 321.373
• Mol File: 159360-04-0.mol

Chemical Properties

• CAS DataBase Reference: (4R,5S)-4-benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5S)-4-benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid methyl ester(159360-04-0)
• EPA Substance Registry System: (4R,5S)-4-benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid methyl ester(159360-04-0)

Safety Data

• Hazardous Substances Data: 159360-04-0(Hazardous Substances Data)

Upstream product

• 79-20-9 acetic acid methyl ester 
• 250039-48-6 (2R,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoic acid pentafluorophenyl ester 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 94284-00-1 methyl (2S,3S)-3-methyl-2-(p-tolyl-sulfonyloxy)pentanoate 
• 488-15-3 (2S,3S)-2-Hydroxy-3-methylpentanoic acid 
• 73-32-5 L-isoleucine 
• 1730-97-8 (S)-2-methylbutyraldehyde 
• 1565-80-6 (2S)-2-methyl-1-butanol 
• 3160-59-6 N-benzyloxycarbonylamino-D-alloisoleucine 
• 57570-85-1 lithium enolate of methyl acetate 
• 56577-28-7 methyl (2S,3S)-2-hydroxy-3-methylpentanoate 
• 60667-85-8 D-allo-isoleucine methyl ester hydrochloride 
• 126886-54-2 methyl (2R,3S)-2-azido-3-methylpentanoate 
• 75315-63-8 N-(benzyloxycarbonyl)succinimide 

Downstream Products

• 159407-39-3 (3S,4R,5S)-4-benzyloxycarbonylamino-3-hydroxy-5-methyl-heptanoic acid methyl ester 
• 250039-54-4 C₆₇H₁₁₁N₅O₁₆Si₂ 
• 345664-71-3 N-Z-prolyl-[Hiv²] didemnin A 
• 345664-75-7 C₆₁H₉₇N₅O₁₅Si 
• 345664-76-8 4-amino-5-methyl-3-triisopropylsilanyloxy-heptanoic 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 
• 250039-53-3 (3S,4R,5S)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (S)-2-methyl-1-pentafluorophenyloxycarbonyl-propyl ester 
• 250039-51-1 (3S,4R,5S)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester 
• 250039-47-5 (3S,4R,5S)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (S)-1-carboxy-2-methyl-propyl ester 
• 250039-50-0 (3S,4R,5S)-4-benzyloxycarbonylamino-5-methyl-3-(triisopropylsilanyloxy) heptanoic acid 
• 250039-49-7 (3S,4R,5S)-4-benzyloxycarbonylamino-5-methyl-3-(triisopropylsilanyloxy) heptanoic acid methyl ester 
• 779313-73-4 (5S,8S,12S,13R,16S,17R,20S,22aS)-16-Amino-13-((S)-sec-butyl)-12-hydroxy-5-isobutyl-8-isopropyl-20-(4-methoxy-benzyl)-17,21-dimethyl-tetradecahydro-9,18-dioxa-3a,6,14,21-tetraaza-cyclopentacyclohenicosene-4,7,10,15,19,22-hexaone 
• 250211-78-0 (-)-tamandarin A 

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.

The first total synthesis of (-)-tamandarin A.

[formula: see text] Tamandarin A (1), a newly isolated natural product similar in structure to didemnin B (2), was shown to be somewhat more active in vitro than 2 against pancreatic carcinoma with an ED50 value 1.5 to 2 ng/mL. We report here the first total synthesis of 1. The key steps include a practical stereoselective synthesis of the Hiv-isostatine unit, high-yielding linear precursor formation, a successful macrocyclization, and coupling of the macrocycle with the side chain to afford tamandarin A (1).

Synthesis of D-Alloisoleucine from L-Isoleucine and from (S)-2-Methylbutan-1-ol. Synthesis of Isostatine

Three different synthetic routes to the uncommon α-amino acid D-alloisoleucine were studied.The first was based on the stereospecific inversion of configuration of the C-2 stereogenic carbon of L-isoleucine.The second involved acetylation of L-isoleucine with epimerization at the C-2 carbon, giving a mixture of L-isoleucine and D-alloisoleucine, which was resolved enzymically with hog kidney acylase.In a new approach, an epimeric mixture of L-isoleucine and D-alloisoleucine was synthesized from (S)-2-methylbutan-1-ol and was again resolved enzymically.The D-alloisoleucine produced in these syntheses was subsequently transformed into the γ-amino acid isostatine.