252981-50-3

Basic information

• Product Name: (4S,7R,8S,9S,13Z,16S)-4,8-Dihydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-[2-(hydroxymethyl)-4-thiazolyl]ethenyl]-1-oxacyclohexadec-13-ene-2,6-dione
• Synonyms: 21-Hydroxyepothilone D; Desoxyepothilone F; dEpoF
• CAS NO: 252981-50-3
• Molecular Formula: C₂₇H₄₁NO₆S
• Molecular Weight: 507.69492
• Mol File: 252981-50-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (4S,7R,8S,9S,13Z,16S)-4,8-Dihydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-[2-(hydroxymethyl)-4-thiazolyl]ethenyl]-1-oxacyclohexadec-13-ene-2,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,7R,8S,9S,13Z,16S)-4,8-Dihydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-[2-(hydroxymethyl)-4-thiazolyl]ethenyl]-1-oxacyclohexadec-13-ene-2,6-dione(252981-50-3)
• EPA Substance Registry System: (4S,7R,8S,9S,13Z,16S)-4,8-Dihydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-[2-(hydroxymethyl)-4-thiazolyl]ethenyl]-1-oxacyclohexadec-13-ene-2,6-dione(252981-50-3)

Safety Data

• Hazardous Substances Data: 252981-50-3(Hazardous Substances Data)

Upstream product

• 346652-33-3 (Z)-(4S,7R,8S,9S,16S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-16-{(E)-2-[2-(tert-butyl-dimethyl-silanyloxymethyl)-thiazol-4-yl]-1-methyl-vinyl}-5,5,7,9,13-pentamethyl-oxacyclohexadec-13-ene-2,6-dione 
• 298702-22-4 (Z)-(4S,7R,8S,9S,16S)-8-Hydroxy-16-[(E)-2-(2-hydroxymethyl-thiazol-4-yl)-1-methyl-vinyl]-5,5,7,9,13-pentamethyl-4-triethylsilanyloxy-oxacyclohexadec-13-ene-2,6-dione 
• 346652-23-1 (3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8,12-pentamethyl-5-oxo-tridec-12-enoic acid (S)-1-{(E)-2-[2-(tert-butyl-dimethyl-silanyloxymethyl)-thiazol-4-yl]-1-methyl-vinyl}-but-3-enyl ester 
• 346652-97-9 2-(tert-butyl-dimethyl-silanyloxymethyl)-4-[3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-5-trimethylsilanyloxy-hexa-1,5-dienyl]-thiazole 
• 346653-04-1 4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxymethyl)-thiazol-4-yl]-5-methyl-hex-5-ene-1,2-diol 
• 252205-67-7 4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxymethyl)-thiazol-4-yl]-1-hydroxy-5-methyl-hex-5-en-2-one 
• 252205-66-6 4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxymethyl)-thiazol-4-yl]-5-methyl-hex-5-en-2-one 
• 252205-68-8 2-(tert-butyl-dimethyl-silanyloxymethyl)-4-[3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-hexa-1,5-dienyl]-thiazole 
• 346652-15-1 3-(tert-butyl-dimethyl-silanyloxy)-5-[2-(tert-butyl-dimethyl-silanyloxymethyl)-thiazol-4-yl]-4-methyl-pent-4-enal 
• 252205-69-9 (E)-(S)-1-[2-(tert-Butyl-dimethyl-silanyloxymethyl)-thiazol-4-yl]-2-methyl-hexa-1,5-dien-3-ol 
• 252205-86-0 (E)-(S)-4-Hydroxy-6-(2-hydroxymethyl-thiazol-4-yl)-5-methyl-hex-5-en-2-one 
• 346653-07-4 (E)-(S)-1-(2-Hydroxymethyl-thiazol-4-yl)-2-methyl-hexa-1,5-dien-3-ol 
• 252205-76-8 (E)-4-Hydroxy-6-(2-hydroxymethyl-thiazol-4-yl)-5-methyl-hex-5-en-2-one 

Downstream Products

• 208518-52-9 Epothilone F 

Relevant articles and documents

Total Synthesis and Antitumor Activity of 12,13-Desoxyepothilone F: An Unexpected Solvolysis Problem at C15, Mediated by Remote Substitution at C21

A new epothilone analogue, 12,13-desoxyepothilone F (dEpoF, 21-hydroxy-12,13-desoxyepothilone B, 21-hydroxyepothilone D), was synthesized and evaluated for antitumor potential. A convergent strategy employed for the semipractical synthesis of 12,13-desoxyepothilone B (dEpoB) has been utilized to yield an amount of dEpoF sufficient for relevant biological studies. The results from an in vitro assay reveal that this new analogue is highly active against various tumor cell lines with a potency comparable to that of dEpoB. In particular, the growth of resistant tumor cells is inhibited by dEpoF at concentrations where paclitaxel (Taxol) is basically ineffective. A preliminary assessment of its in vivo activity is also promising. The new analogue, containing an additional hydroxyl group at C21, exhibits advantages over other epothilones in terms of water solubility, and can serve as a readily functionalizable handle to produce other useful compounds for pertinent biological studies.

Catalytic antibody route to the naturally occurring epothilones: Total synthesis of epothilones A-F

Naturally occurring epothilones have been synthesized starting from enantiomerically pure aldol compounds 9-11, which were obtained by antibody catalysis. Aldolase antibody 38C2 catalyzed the resolution of (±)-9 by enantioselective retro-aldol reaction to afford 9 in 90% ee at 50% conversion. Compounds 10 and 11 were obtained in more than 99% ee at 50% conversion by resolution of their racemic mixtures using newly developed aldolase antibodies 84G3, 85H6 or 93F3. Compounds 9, 10 and 11 were resolved in multigram quantities and then converted to the epothilones by metathesis processes, which were catalyzed by Grubbs' catalysts.