193146-49-5 Usage
Description
(3S,6R,7S,8S,12Z,15S,16E)-1,3,15-TRIS-[TERT-BUTYL(DIMETHYL)SILYL]OXY-7-HYDROXY-4,4,6,8,12,16-HEXAMETHYL-17-(2-METHYL-1,3-THIAZOL-4-YL)HEPTADECYL-12,16-DIEN-5-ONE is a complex organic compound with a unique molecular structure. It is characterized by its multiple stereocenters and functional groups, which contribute to its chemical properties and potential applications.
Uses
Used in Pharmaceutical Industry:
(3S,6R,7S,8S,12Z,15S,16E)-1,3,15-TRIS-[TERT-BUTYL(DIMETHYL)SILYL]OXY-7-HYDROXY-4,4,6,8,12,16-HEXAMETHYL-17-(2-METHYL-1,3-THIAZOL-4-YL)HEPTADECYL-12,16-DIEN-5-ONE is used as an intermediate in the synthesis of Epothilones for the pharmaceutical industry. Epothilones are polyketide natural products that inhibit cancer cells by a mechanism similar to paclitaxel and are effective against paclitaxel-resistant tumors. Epothilone D, a derivative, is in phase I clinical testing in patients with advanced solid tumors. It is a cytotoxic macrolide that stabilizes malignant cells' microtubules and arrests mitosis, a characteristic it shares with other epothilones. They bind to the same hepatic sites as does paclitaxel (Taxol) in a 1:1 stoichiometric ratio of α, β-tubulin heterodimers.
Chemical Properties:
(3S,6R,7S,8S,12Z,15S,16E)-1,3,15-TRIS-[TERT-BUTYL(DIMETHYL)SILYL]OXY-7-HYDROXY-4,4,6,8,12,16-HEXAMETHYL-17-(2-METHYL-1,3-THIAZOL-4-YL)HEPTADECYL-12,16-DIEN-5-ONE is a colorless oil, indicating its potential for use in various chemical reactions and applications due to its liquid state at room temperature.
Check Digit Verification of cas no
The CAS Registry Mumber 193146-49-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,9,3,1,4 and 6 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 193146-49:
(8*1)+(7*9)+(6*3)+(5*1)+(4*4)+(3*6)+(2*4)+(1*9)=145
145 % 10 = 5
So 193146-49-5 is a valid CAS Registry Number.
193146-49-5Relevant 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
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, (2015/06/25)
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 Syntheses of Epothilones B and D
Mulzer, Johann,Mantoulidis, Andreas,Oehler, Elisabeth
, p. 7456 - 7467 (2007/10/03)
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.
Easy access to the epothilone family - Synthesis of epothilone B
Mulzer, Johann,Mantoulidis, Andreas,Oehler, Elisabeth
, p. 8633 - 8636 (2007/10/03)
An easy access to four out of five naturally occurring epothilones (A- E, 1-5) is reported. Key steps are an enantioselective Mukaiyama type aldol reaction, (E)- and (Z)-selective olefinations, and a sulfone alkylation.
