(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

Base Information Edit

Chemical Name:(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
CAS No.:193146-49-5
Molecular Formula:C45H86NO5SSi3 *
Molecular Weight:838.512
Hs Code.:
Mol file:193146-49-5.mol

(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

Synonyms:(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

Suppliers and Price of (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

Supply Marketing:Edit

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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TRC
(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
0.5mg
$ 140.00

Total 2 raw suppliers

Chemical Property of (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 Edit

Chemical Property:

PSA：106.12000
LogP:13.78260
Solubility.:Acetone, Chloroform, Dichloromethane, Ethanol, Ethyl Acetate, Hexane, Methanol

Purity/Quality:

98% ^*data from raw suppliers

(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 ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Uses An intermediate in the synthesis of Epothilones. Epothilones are polyketide natural products that inhibit cancer cells by a mechanism similar to paclitaxel, and also are effective against paclitaxel- resistant tumours. Epothilone D is in phase I clinical testing of in patients with advanced solid tumours. Epothilone D is a cytotoxic macrolide that stabilises malignant cells' microtubules and arr ests 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 a, b-tubulin heterodimers. An intermediate in the synthesis of Epothilones. Epothilones are polyketide natural products that inhibit cancer cells by a mechanism similar to paclitaxel, and also are effective against paclitaxel-resistant tumours. Epothilone D is in phase I clinical testing of in patients with advanced solid tumours. Epothilone D is a cytotoxic macrolide that stabilises 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 a, b-tubulin heterodimers.

Technology Process of (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

There total 74 articles about (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 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 6436-59-5
ethyl 2-methylthiazole-4-carboxylate

: 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

Guidance literature:: Multi-step reaction with 16 steps

1: 90 percent / DIBAL / CH₂Cl₂ / 1 h / -78 °C

2: 98 percent / benzene / 2 h / Heating

3: 74 percent / diethyl ether; pentane / 1 h / -100 °C

4: 99 percent / imidazole / dimethylformamide / 1) 0 deg C, 45 min, 2) 25 deg C, 2.5 h

5: 95 percent / 4-methylmorpholine N-oxide, OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 1) 0 deg C, 2.5 h, 2) 25 deg C, 12 h

6: 98 percent / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C

7: 95 percent / benzene / 3 h / Heating

8: 98 percent / DIBAL / tetrahydrofuran; CH₂Cl₂ / 3 h / -78 °C

9: 83 percent / Ph₃P, CCl₄ / 24 h / 100 °C

10: 99 percent / LiEt₃BH / tetrahydrofuran / 1 h / 0 °C

11: 91 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C

12: 92 percent / I₂, imidazole, Ph₃P / diethyl ether; acetonitrile / 0.5 h / 0 °C

13: 1) LDA / 1) THF, 0 deg C, 8 h, 2) THF, -100 deg C -> -20 deg C, 10 h

14: 80 percent / monoperoxyphthalic acid magnesium salt / methanol / 1 h / 0 °C

15: 82 percent / DIBAL / toluene / 1 h / -78 °C

16: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min

With 1H-imidazole; lead(IV) acetate; tetrachloromethane; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; iodine; diisobutylaluminium hydride; lithium triethylborohydride; 4-methylmorpholine N-oxide; Monoperoxyphthalic acid, magnesium salt; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; pentane; benzene;
DOI:10.1021/ja971110h

Reference yield:

: 187527-25-9
(-)-(5S)-5,7-bis{[tert-butyl(dimethyl)silyl]oxy}-4,4-dimethylheptan-3-one

: 193146-27-9
(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-dienal

: 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

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -95 ℃; for 2h; Yield given;
DOI:10.1016/S0040-4039(98)02026-7

Reference yield:

: 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

: 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

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / NiCl₂; CrCl₂ / dimethylformamide / 0.67 h / 20 °C

2: 87 percent / SOCl₂ / diethyl ether; pentane / 6.5 h / -78 - 0 °C

3: 88 percent / LiEt₃BH / tetrahydrofuran / 2 h / -78 - 20 °C

4: 80 percent / PCC

5: LDA

With chromium dichloride; thionyl chloride; lithium triethylborohydride; pyridinium chlorochromate; nickel dichloride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ol010094x