118477-03-5

Basic information

• Product Name: bengamide E
• Synonyms: bengamide E;(2R,3R,4S,5R,6E)-3,4,5-Trihydroxy-2-methoxy-8-methyl-N-[[(3S)-hexahydro-2-oxo-1H-azepin]-3β-yl]-6-nonenamide
• CAS NO: 118477-03-5
• Molecular Formula: C₁₇H₃₀N₂O₆
• Molecular Weight: 358.4299
• Mol File: 118477-03-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 689.4°Cat760mmHg
• Flash Point: 370.7°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 5.39E-22mmHg at 25°C
• Refractive Index: 1.54
• PKA: 12.65±0.20(Predicted)
• CAS DataBase Reference: bengamide E(CAS DataBase Reference)
• NIST Chemistry Reference: bengamide E(118477-03-5)
• EPA Substance Registry System: bengamide E(118477-03-5)

Safety Data

• Hazardous Substances Data: 118477-03-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C17H30N2O6/c1-10(2)7-8-12(20)13(21)14(22)15(25-3)17(24)19-11-6-4-5-9-18-16(11)23/h7-8,10-15,20-22H,4-6,9H2,1-3H3,(H,18,23)(H,19,24)/b8-7+/t11-,12+,13-,14+,15+/m0/s1

Upstream product

• 21568-87-6 2-aminocaprolactam 

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.