1414867-04-1

Basic information

• Product Name: (2S,4R,5R,8R,E)-2-nonyl-10-oxo-3,4,5,8,9,10-hexahydro-2H-oxecine-4,5,8-triyl tris(4-bromobenzoate)
• CAS NO: 1414867-04-1
• Molecular Weight: 877.462
• Mol File: 1414867-04-1.mol

Chemical Properties

• CAS DataBase Reference: (2S,4R,5R,8R,E)-2-nonyl-10-oxo-3,4,5,8,9,10-hexahydro-2H-oxecine-4,5,8-triyl tris(4-bromobenzoate)(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4R,5R,8R,E)-2-nonyl-10-oxo-3,4,5,8,9,10-hexahydro-2H-oxecine-4,5,8-triyl tris(4-bromobenzoate)(1414867-04-1)
• EPA Substance Registry System: (2S,4R,5R,8R,E)-2-nonyl-10-oxo-3,4,5,8,9,10-hexahydro-2H-oxecine-4,5,8-triyl tris(4-bromobenzoate)(1414867-04-1)

Safety Data

• Hazardous Substances Data: 1414867-04-1(Hazardous Substances Data)

Upstream product

• 1414867-06-3 (1S,2R)-1-((2S,3S)-3-nonyloxiran-2-yl)-2-(trityloxy)but-3-en-1-ol 
• 1414866-97-9 (3R,4R,6S)-pentadec-1-ene-3,4,6-triol 
• 1414866-98-0 (S)-1-((4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)undecan-2-ol 
• 1414867-01-8 ((S)-1-((4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)undecan-2-yl) (R)-3-(tert-butyldimethylsilyloxy)pent-4-enoate 
• 1414867-05-2 (3R,4R,E)-3-(trityloxy)pentadeca-1,5-dien-4-ol 
• 1414867-03-0 (3aR,5S,9R,11aR,E)-9-hydroxy-2,2-dimethyl-5-nonyl-4,5,8,9-tetrahydro-3aH-[1,3]dioxolo[4,5-d]oxecin-7(11aH)-one 
• 1414867-16-5 (+)-(3R,6R,7R,9S)-seimatopolide A 
• 586-75-4 4-chlorobenzoyl chloride 

Relevant articles and documents

Total syntheses of naturally occurring seimatopolide A and its enantiomer from chiral pool starting materials using a bidirectional strategy

Enantioselective total syntheses of both enantiomers of the recently isolated decanolide natural product seimatopolide A are described. The C 2-symmetric building blocks (R,R)-hexa-1,5-diene-3,4-diol (derived from d-mannitol) and its enantiomer (derived from l-(+)-tartrate) serve as key starting materials, which are elaborated in a bidirectional way using a selective mono-cross-metathesis, regio-and stereoselective epoxidation, and regioselective reductive epoxide opening to furnish the first fragment. Both enantiomers of the second fragment, 3-hydroxypent-4-enoic acid, were conveniently obtained through a lipase-catalyzed kinetic resolution and merged with the first fragment via Shiina esterification. An E-selective ring-closing metathesis was used to access the 10-membered lactone. A comparison of the specific optical rotations of synthetic seimatopolides with those reported for the natural product suggests that the originally assigned (3R,6R,7R,9S)- configuration should be corrected to (3S,6S,7S,9R).