308357-83-7

Basic information

• Product Name: (3S)-5-hydroxy-3-[(4-methoxybenzyl)oxy]pentan-2-one
• Synonyms: (3S)-5-hydroxy-3-[(4-methoxybenzyl)oxy]pentan-2-one
• CAS NO: 308357-83-7
• Molecular Weight: 238.284
• Mol File: 308357-83-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3S)-5-hydroxy-3-[(4-methoxybenzyl)oxy]pentan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-5-hydroxy-3-[(4-methoxybenzyl)oxy]pentan-2-one(308357-83-7)
• EPA Substance Registry System: (3S)-5-hydroxy-3-[(4-methoxybenzyl)oxy]pentan-2-one(308357-83-7)

Safety Data

• Hazardous Substances Data: 308357-83-7(Hazardous Substances Data)

Upstream product

• 917-54-4 methyllithium 
• 308357-84-8 (-)-(3S)-3-[(4-methoxybenzyl)oxy]dihydrofuran-2(3H)-one 

Downstream Products

• 308357-90-6 (-)-(3S,6R,7S,8S,12Z,15S,16E)-1,3,7-tris{[tert-butyl(dimethyl)silyl]oxy}-15-[(4-methoxybenzyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one 
• 308357-88-2 (3S,6R,7S,8S,12Z,15S,16E)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-7-hydroxy-15-[(4-methoxybenzyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one 
• 308357-91-7 (3S,6R,7S,8S,12Z,15S,16E)-3,7-bis{[tert-butyl(dimethyl)silyl]oxy}-1-hydroxy-15-[(4-methoxybenzyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one 
• 308357-92-8 (12Z,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienal 
• 308357-86-0 4-{(1E,3S,5Z,10S)-11-{[tert-butyl(diphenyl)silyl]oxy}-3-[(4-methoxybenzyl)oxy]-2,6,10-trimethylundeca-1,5-dienyl}-2-methyl-1,3-thiazole 
• 308357-93-9 (3S,6R,7S,8S,12Z,15S,16E)-3,7-bis{[tert-butyl(dimethyl)silyl]oxy}-15-[(4-methoxybenzyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid 
• 308357-85-9 4-[(1E,3S,5Z,8R/S,10S)-11-{[tert-butyl(diphenyl)silyl]oxy}-3-[(4-methoxybenzyl)oxy]-2,6,10-trimethyl-8-(phenylsulfonyl)undeca-1,5-dienyl]-2-methyl-1,3-thiazole 
• 308357-87-1 (2S,6Z,9S,10E)-9-[(4-methoxybenzyl)oxy]-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dien-1-ol 
• 308357-89-3 (2S,6Z,9S,10E)-9-[(4-methoxybenzyl)oxy]-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal 
• 198768-52-4 ethyl (2Z,5S,6E)-5-[(4-methoxybenzyl)oxy]-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienoate 
• 198768-55-7 (-)-(2Z,5S,6E)-5-[(4-methoxybenzyl)oxy]-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dien-1-ol 
• 1027920-39-3 (3S,4E)-3-[(4-methoxybenzyl)oxy]-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-al 
• 198768-54-6 (3S,4E)-3-[(4-methoxybenzyl)oxy]-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-ol 

Relevant articles and documents

Total Syntheses of Epothilones B and D

Total syntheses of the microtubule stabilizing antitumor drugs epothilone B and D are described, starting from optically pure (S)-malic acid and methyl (R)-3-hydroxy-2-methylpropionate. The synthesis is highly convergent by coupling the three fragments C1-C6 (fragment D), C7-C10 (fragment C), and C11-C21 (fragment B). Key steps are two stereoselective Wittig type olefinations to generate the 12,13- and 16,17-double bonds, an enantioselective Mukaiyama aldol addition to synthesize fragment D, and a sulfone anion allyl iodide alkylation to connect fragments B and C. Finally fragment D was attached to the B + C fragment via aldol addition.