198768-55-7

Upstream product

• 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 
• 39238-07-8 4-(chloromethyl)-2-methyl-1,3-thiazole 
• 198768-51-3 4-{(1E)-2-[(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]prop-1-enyl}-2-methyl-1,3-thiazole 
• 308357-83-7 (3S)-5-hydroxy-3-[(4-methoxybenzyl)oxy]pentan-2-one 
• 198768-54-6 (3S,4E)-3-[(4-methoxybenzyl)oxy]-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-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 
• 198768-47-7 (-)-methyl 1-{(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl}-4-carboxylate 
• 198768-49-9 (-)-1-[(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]ethanone 
• 308357-84-8 (-)-(3S)-3-[(4-methoxybenzyl)oxy]dihydrofuran-2(3H)-one 

Downstream Products

• 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 
• 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 
• 308357-85-9 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 
• 308357-93-9 (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 
• 308357-86-0 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 
• 308357-92-8 (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 
• 308357-91-7 (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 
• 308357-88-2 (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 
• 308357-90-6 (-)-(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 

Relevant academic research and scientific papers

Thiazole derivatives, method for their production and use

Thiazole derivatives of formula II, in which R1means C1-C4alkyl, R2means any protective group that can be chelated, R3means hydrogen or C1-C4alkyl, Y means CO2R4, CHO, CH—CH2or CH2R5, whereby R4stands for C1-C4alkyl and an optionally substituted benzyl group, R5stands for halogen, hydroxy, p-toluenesulfonate and —OSO2B and B stands for C1-C4alkyl or C1-C4perfluoroalkyl, can be produced free of diastereomers and are suitable for the production of epothilone A and epothilone B and derivatives thereof.

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.

Synthesis of the C(11)-C(20) segment of the cytotoxic macrolide epothilone B

Compound 11, representing the C(11)-C(20) segment of the macrolide epothilone B (1b) has been prepared using two Wittig reactions and a Sharpless asymmetric epoxidation as the key steps.