118878-58-3

Basic information

• Product Name: (3S,4R,5S)-N-(9-Fluorenylmethoxycarbonyl)isostatine
• CAS NO: 118878-58-3
• Molecular Weight: 397.471
• Mol File: 118878-58-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (3S,4R,5S)-N-(9-Fluorenylmethoxycarbonyl)isostatine(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R,5S)-N-(9-Fluorenylmethoxycarbonyl)isostatine(118878-58-3)
• EPA Substance Registry System: (3S,4R,5S)-N-(9-Fluorenylmethoxycarbonyl)isostatine(118878-58-3)

Safety Data

• Hazardous Substances Data: 118878-58-3(Hazardous Substances Data)

Upstream product

• 118878-56-1 Methyl (4S,5S)-4-(9-fluorenylmethoxycarbonylamino)-5-methyl-3-oxoheptanoate 
• 118878-65-2 N-(9-Fluorenylmethoxycarbonyl)-D-alloisoleucine methyl ester 
• 118904-37-3 N-(9-Fluorenylmethoxycarbonyl)-D-alloisoleucine 
• 118878-54-9 (4S,5S)-4-(9-Fluorenylmethoxycarbonylamino)-5-methyl-3-oxoheptanoyl chloride 
• 118878-57-2 (3S,4R,5S)-N-(9-Fluorenylmethoxycarbonyl)isostatine methyl ester 
• 129867-96-5 tert-butyl (3S,4R,5S)-4-(9-fluorenylmethoxycarbonylamino)-3-hydroxy-5-methylheptanoate 

Downstream Products

• 118878-63-0 C₅₇H₈₂Cl₃N₅O₁₆ 
• 118878-63-0 C₅₇H₈₂Cl₃N₅O₁₆ 

Relevant articles and documents

TOTAL SYNTHESIS OF THE DIDEMNINS - 1. SYNTHESIS OF THE PEPTOLIDE RING

The 23-membered peptolide ring of the didemnins is formed in a two phase cyclization of a linear ω-amino-pentafluorophenyl ester in 70percent yield without high dilution. (2RS,4S)-2,5-dimethyl-4-hydroxy-3-oxohexanoic acid (Hip) and (3S,4R,5S)-isostatine are synthesized by acylations of trimethylsilyl malonates.

Total Synthesis of the Didemnins; III. - Synthesis of Protected (2R,3S)-Alloisoleucine and (3S,4R,5S)-Isostatine Derivatives - Amino Acids from Hydroxy Acids

(2S,3S)-2-Acetoxy-3-methylvaleric acid (3) is prepared from L-isoleucine (2) with 96percent retention of configuration.Compound 3 is converted to optically pure methyl D-alloisoleucinate (7) as its hydrochloride salt, via the methanesulfonate 5 and the azide 6 with 76percent yield and 99.9percent inversion.Subsequent protection-saponification-activation of 7, followed by reaction with the lithium enolate of methyl trimethylsilyl malonate and reduction, yields (3S,4R,5S)-N-(9-fluorenylmethoxycarbonyl)isostatine (12). (3S,4R,5S)-Isostatine is a characteristic unit of the didemnines 1.