294198-49-5

Basic information

• Product Name: (4R,5S)-4-benzyloxy-5-tert-butyldimethylsilyloxy-2(E)-hexenoic acid
• Synonyms: (4R,5S)-4-benzyloxy-5-tert-butyldimethylsilyloxy-2(E)-hexenoic acid
• CAS NO: 294198-49-5
• Molecular Weight: 350.53
• Mol File: 294198-49-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (4R,5S)-4-benzyloxy-5-tert-butyldimethylsilyloxy-2(E)-hexenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5S)-4-benzyloxy-5-tert-butyldimethylsilyloxy-2(E)-hexenoic acid(294198-49-5)
• EPA Substance Registry System: (4R,5S)-4-benzyloxy-5-tert-butyldimethylsilyloxy-2(E)-hexenoic acid(294198-49-5)

Safety Data

• Hazardous Substances Data: 294198-49-5(Hazardous Substances Data)

Upstream product

• 294198-48-4 methyl (4R,5S)-4-benzyloxy-5-tert-butyldimethylsilyloxy-2(E)-hexenoate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 183625-29-8 methyl (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate 

Downstream Products

• 295788-39-5 2,2,2-trichloroethyl (4R,5S)-4-benzyloxy-5-tert-butyldimethylsilyloxy-2(E)-hexenoate 
• 294198-51-9 (E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester 
• 473555-54-3 methyl (3S,8R,9S)-8-benzyloxy-9-tert-butyldimethylsiloxy-3-methyl-5-oxo-4-oxadeca (6E)-enoate 
• 473555-50-9 methyl (3R,8R,9S)-8-benzyloxy-9-tert-butyldimethylsiloxy-3-methyl-5-oxo-4-oxadeca (6E)-enoate 
• 459809-75-7 (E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-4-methoxycarbonyl-1-methyl-but-3-enyl ester 
• 434938-18-8 (E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl ester 
• 473555-52-1 methyl (3R,8R,9S,14R,15S)-8,14-dibenzyloxy-15-tert-butyldimethylsiloxy-3,9-dimethyl-5,11-dioxo-4,10-dioxadeca (6E,12E)-dienoate 
• 473555-56-5 methyl (3S,8R,9S,14R,15S)-8,14-dibenzyloxy-15-tert-butyldimethylsiloxy-3,9-dimethyl-5,11-dioxo-4,10-dioxadeca (6E,12E)-dienoate 
• 459809-90-6 (E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (S)-2-((E)-(1S,2R)-2-benzyloxy-4-methoxycarbonyl-1-methyl-but-3-enyloxycarbonyl)-1-methyl-ethyl ester 
• 434938-20-2 (E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-[(S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethoxycarbonyl]-but-3-enyl ester 
• 434938-26-8 (E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (S)-2-[(E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyloxycarbonyl]-1-methyl-ethyl ester 
• 473555-51-0 (E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (R)-2-methoxycarbonyl-1-methyl-ethyl ester 
• 459809-73-5 (E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (S)-2-methoxycarbonyl-1-methyl-ethyl ester 
• 294198-57-5 (-)-dibenzyl macrosphelide A 

Relevant articles and documents

Formal total synthesis of (+)-macrosphelide A based on regioselective hydrolysis using lipase.

Three kinds of seco-macrosphelide A congeners, (4R,5S,10R,11S,15S)-6, (4R,5S,9S,14R,15S)-7 and (3S,8R,9S,14R,15S)-8 were chemically synthesized, and they were exposed to the lipase OF-360 from Candida rugosa to give three hydroxy carboxylic acids, respectively. Macrolactonization of the hydroxy acid (4R,5S,10R,11S)-18 derived from (4R,5S,10R,11S,15S)-6 gave 12-membered lactone (19) in 47% overall yield from 6, while that of the seco-acid (4) derived from (4R,5S,9S,14R,15S)-7 afforded (-)-dibenzyl macrosphelide A (25) in 27% overall yield from 7. Macrolactonization of the hydrolysis product, seco-acid (5) derived from (3S,8R,9S,14R,15S)-8, provided (-)-dibenzyl macrosphelide A (25) (5% overall yield from 8) and 12-membered lactone (19) (20% overall yield from 8) concurrently.