442913-30-6

Basic information

• Product Name: tert-butyl (2S)-2-[(1,1-diphenylmethylidene)amino]-4-[(2S)-oxiran-2-yl]butanoate
• Synonyms: tert-butyl (2S)-2-[(1,1-diphenylmethylidene)amino]-4-[(2S)-oxiran-2-yl]butanoate
• CAS NO: 442913-30-6
• Molecular Weight: 365.472
• Mol File: 442913-30-6.mol

Chemical Properties

• CAS DataBase Reference: tert-butyl (2S)-2-[(1,1-diphenylmethylidene)amino]-4-[(2S)-oxiran-2-yl]butanoate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (2S)-2-[(1,1-diphenylmethylidene)amino]-4-[(2S)-oxiran-2-yl]butanoate(442913-30-6)
• EPA Substance Registry System: tert-butyl (2S)-2-[(1,1-diphenylmethylidene)amino]-4-[(2S)-oxiran-2-yl]butanoate(442913-30-6)

Safety Data

• Hazardous Substances Data: 442913-30-6(Hazardous Substances Data)

Upstream product

• 81477-94-3 N-(diphenylmethylene)glycine tert-butyl ester 
• 99700-70-6 (S)-(-)-4-iodo-1,2-epoxybutane 

Downstream Products

• 442913-34-0 (3S,6S)-6-[((2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-(phenylmethoxy)non-6-enoyl)amino]-2,3,4,5,6,7-hexahydro-1-methyl-7-oxoazepin-3-yl acetate 
• 442913-42-0 tertbutyl (2S,5S)-2-amino-5-hydroxy-6-(N-methyl-N-phenylmethylamino)hexanoate 
• 104947-69-5 bengamide B 
• 442913-31-7 tert-butyl (2S,5S)-2-[(1,1-diphenylmethylidene)amino]-5-hydroxy-6-[methyl(phenylmethyl)amino]hexanoate 

Relevant articles and documents

The development of a convergent and efficient enantioselective synthesis of the bengamides via a common polyol intermediate

An efficient, general synthetic route to the bengamide family of antitumor agents from a common polyol thioester is described. Consecutive aldol condensations afford the protected polyol thioester side chain suitable for coupling to the bengamides. A novel chiral-phase-transfer-catalyzed enantioselective alkylation affords the properly functionalized caprolactams required for the synthesis of more-complex members of the bengamide family. Use of the methyl 2-naphthyl ether protecting group, compatible with the boron Lewis acids required for enantioselective aldol condensation, allows direct access to all the bengamides.

A Practical Enantioselective Total Synthesis of the Bengamides B, E, and Z

(equation presented) A practical total synthesis of Bengamides B, E, and Z from a common polyol intermediate is described. Consecutive aldol condensations afford a protected polyol thioester side chain suitable for coupling to the Bengamides. A novel chiral phase transfer catalyzed enantioselective alkylation affords the more highly functionalized amino caprolactams required for Bengamides B and Z. Use of the 2-naphthylmethyl ether protecting group, compatible with the boron Lewis acids required for enantioselective aldol condensation, allows direct access to Bengamide B.