198955-38-3

Basic information

• Product Name: 1',26-bis-O-(1,1-dimethylethyl)dimethylsilyl-3,5:7,9:11,13-tris-O-(1-methylethylidine)-15-O-triisopropylsiloxy-filipin III
• Synonyms: 1',26-bis-O-(1,1-dimethylethyl)dimethylsilyl-3,5:7,9:11,13-tris-O-(1-methylethylidine)-15-O-triisopropylsiloxy-filipin III
• CAS NO: 198955-38-3
• Molecular Weight: 1159.9
• Mol File: 198955-38-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1',26-bis-O-(1,1-dimethylethyl)dimethylsilyl-3,5:7,9:11,13-tris-O-(1-methylethylidine)-15-O-triisopropylsiloxy-filipin III(CAS DataBase Reference)
• NIST Chemistry Reference: 1',26-bis-O-(1,1-dimethylethyl)dimethylsilyl-3,5:7,9:11,13-tris-O-(1-methylethylidine)-15-O-triisopropylsiloxy-filipin III(198955-38-3)
• EPA Substance Registry System: 1',26-bis-O-(1,1-dimethylethyl)dimethylsilyl-3,5:7,9:11,13-tris-O-(1-methylethylidine)-15-O-triisopropylsiloxy-filipin III(198955-38-3)

Safety Data

• Hazardous Substances Data: 198955-38-3(Hazardous Substances Data)

Upstream product

• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 
• 198955-37-2 1',26-bis-O-(1,1-dimethylethyl)dimethylsilyl-3,5:7,9:11,13-tris-O-(1-methylethylidine)filipin III 

Downstream Products

• 480-49-9 15-Deoxylagosin 

Relevant articles and documents

Total synthesis of Filipin III

Filipin III (1), a polyene macrolide antibiotic, has been synthesized for the first time. The polyol chain was assembled using a stereoselective carbon-carbon bond forming strategy previously developed in our lab: a cyanohydrin acetonide alkylation and reductive decyanation sequence. The polyene segment was prepared from L-ascorbic acid. These two components were coupled using Yamaguchi's esterification, and cyclized with an intramolecular Horner-Emmons reaction to form a trisubstituted alkene. Stereoselective reduction followed by deprotection gave filipin III. This highly convergent approach to filipin III represents the first total synthesis of a methylpentaene macrolide antibiotic.