210690-99-6

Basic information

• Product Name: (+)-(2S,6Z,9S,10E)-9-{[tert-Butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)-undeca-6,10-dien-1-ol
• Synonyms: (+)-(2S,6Z,9S,10E)-9-{[tert-Butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)-undeca-6,10-dien-1-ol;(2S,6Z,9S,10E)-9-[[(1,1-DiMethylethyl)diMethylsilyl]oxy]-2,6,10-triMethyl-11-(2-Methyl-4-thiazolyl)-6,10-undecadien-1-ol
• CAS NO: 210690-99-6
• Molecular Formula: C₂₄H₄₃NO₂SSi
• Molecular Weight: 437.75422
• Product Categories: Chiral Reagents
• Mol File: 210690-99-6.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Dichloromethane, Ethanol, Ethyl Acetate, Methanol, Toluene
• CAS DataBase Reference: (+)-(2S,6Z,9S,10E)-9-{[tert-Butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)-undeca-6,10-dien-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(2S,6Z,9S,10E)-9-{[tert-Butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)-undeca-6,10-dien-1-ol(210690-99-6)
• EPA Substance Registry System: (+)-(2S,6Z,9S,10E)-9-{[tert-Butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)-undeca-6,10-dien-1-ol(210690-99-6)

Safety Data

• Hazardous Substances Data: 210690-99-6(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

Upstream product

• 210690-85-0 (2S,6Z,9S,10E)-1,9-Bis[(1,1-dimethylethyl)dimethylsilyloxy]-11-(2-methylthiazol-4-yl)-2,6,10-trimethyl-undeca-6,10-diene 
• 39238-07-8 4-(chloromethyl)-2-methyl-1,3-thiazole 
• 121587-29-9 (3S)-3-methyl-1-phenylsulfonylbutan-4-ol 
• 164264-14-6 (3S)-3-[(1,1-Dimethylethyl)dimethylsilyloxy]-oxolan-2-one 
• 188899-14-1 (3S,4E)-3-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-ol 
• 188730-08-7 (3S,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-al 
• 218615-21-5 (3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-hydroxypentan-2-one 
• 218613-98-0 (-)-(3S)-4-{[tert-butyl(dimethyl)silyl]oxy}-3-methylbutyl phenyl sulfone 
• 218614-07-4 4-((1E,3S,5Z)-3-{[tert-butyl(dimethyl)silyl]oxy}-7-iodo-2,6-dimethylhepta-1,5-dienyl)-2-methyl-1,3-thiazole 
• 218614-16-5 (-)-(2Z,5S,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dien-1-ol 
• 218614-04-1 ethyl (2Z,5S,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienoate 
• 308357-81-5 4-[(1E,3S,5Z,8R/S,10S)-3,11-bis{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-8-(phenylsulfonyl)undeca-1,5-dienyl]-2-methyl-1,3-thiazole 
• 263900-30-7 (-)-(3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methylbutyl phenyl sulfone 
• 5673-98-3 (S)-(-)-2-methyl-4-penten-1-ol 

Downstream Products

• 152044-54-7 epothilone B 
• 189453-35-8 (4S,7R,8S,9S,13Z,16S,1'E)-4,8-di-tert-butyldimethylsilyloxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-1-oxa-13-cyclohexadecene-2,6-dione 
• 189453-10-9 epothilone D 
• 193146-53-1 (5S,8R,9S,10S,17S,Z)-9-(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-2,2,3,3,6,6,8,10,14,19,19,20,20-tridecamethyl-17-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,18-dioxa-3,19-disilahenicos-14-en-7-one 
• 193146-51-9 (7S,10R,11S,12S,19S,Z)-7,11-bis(tert-butyldimethylsilyloxy)-2,2,3,3,8,8,10,12,16,21,21,22,22-tridecamethyl-19-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,20-dioxa-3,21-disilatricos-16-en-9-one 
• 193146-49-5 (7S,10R,11S,12S,19S,Z)-7-(tert-butyldimethylsilyloxy)-11-hydroxy-2,2,3,3,8,8,10,12,16,21,21,22,22-tridecamethyl-19-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,20-dioxa-3,21-disilatricos-16-en-9-one 
• 193146-63-3 (12Z,16E)-(3S,6R,7S,8S,15S)-3,7,15-tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienoic acid 
• 193146-26-8 (3S,6R,7S,8S,12Z,15S,16E)-3,7-bis{[tert-butyl(dimethyl)silyl]oxy}-15-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid 
• 219989-84-1 ixabepilone 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF (1S,3S,7S,10R,11S,12S,16R)-7,11-DIHYDROXY-8,8,10,12,16-PENTAMETHYL-3-[(1E)-1-METHYL-2-(2-METHYL-4-THIAZOLYL)ETHENYL]-17-OXA-4-AZABICYCLO[14.1.0]HEPTADECANE-5,9-DIONE AND INTERMEDIATES THEREOF

The present invention relates to an improved process for the preparation of (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-methyl-2-(2- methyl-4-thiazolyl)ethenyl]- 17-oxa-4-azabicyclo[ 14.1.0]heptadecane-5,9-dione represented by the following structural formula I and intermediates thereof. The present invention also provides novel intermediate compounds useful for the preparation of compound of formula I and its intermediates.

Total synthesis of epothilone D by sixfold ring cleavage of cyclopropanol intermediates

The ring-opening or ring fragmentation reactions of cyclopropanol intermediates are used in the total synthesis of epothilone D for the creation of trisubstituted double bonds, an ethyl ketone functionality, as well as for the protection of carboxylic and ester groups. Epothilone D is obtained in 1.6% overall yield (24 steps in the longest linear sequence) starting from (R)-methyl 2,3-O-isopropylideneglycerate. The key cyclopropanol intermediates are efficiently obtained by titanium(IV)-catalyzed reactions of readily available esters with Grignard reagents. Crown Copyright

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.