(12E,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid

Base Information

• Chemical Name: (12E,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid
• CAS No.: 201136-77-8
• Molecular Formula: C₅₈H₈₅NO₇SSi₂
• Molecular Weight: 996.552

Synonyms:(12E,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid

Chemical Property of (12E,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (12E,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid

There total 1 articles about (12E,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid 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: 89.0%

(12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid → (12E,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid (201136-77-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 8h;

DOI:10.1039/a705845d

Reference yield:

(12E,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid (201136-77-8) → (E)-(4S,7R,8S,9S,16S)-13-Benzyloxymethyl-4,8-dihydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-ene-2,6-dione

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) Et₃N, 2,4,6-trichlorobenzoyl chloride, 2.) 4-dimethylaminopyridine / 1.) THF, 0 deg C, 1 h, 2.) THF, toluene, 75 deg C, 3 h

2: 69 percent / formic acid / diethyl ether / 1.) -10 deg C, 10 min, 2.) -5 deg C, 3 h

3: 40 percent / NaH, Bu₄NI / tetrahydrofuran / 3.5 h / -15 - 20 °C

4: 90 percent / HF*pyridine / tetrahydrofuran / 24 h / 0 - 25 °C

With dmap; formic acid; 2,4,6-trichlorobenzoyl chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; pyridine hydrogenfluoride; triethylamine; In tetrahydrofuran; diethyl ether;

DOI:10.1016/S0040-4020(98)00352-4

Reference yield:

(12E,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid (201136-77-8) → Benzoic acid (E)-(2S,9S,10S,11R,14S)-10,14-dihydroxy-9,11,13,13-tetramethyl-2-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-12,16-dioxo-oxacyclohexadec-4-en-5-ylmethyl ester

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Et₃N, 2,4,6-trichlorobenzoyl chloride, 2.) 4-dimethylaminopyridine / 1.) THF, 0 deg C, 1 h, 2.) THF, toluene, 75 deg C, 3 h

2: 78 percent / HF*pyridine / tetrahydrofuran / 24 h / Ambient temperature

3: 90 percent / 4-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

With dmap; 2,4,6-trichlorobenzoyl chloride; pyridine hydrogenfluoride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(98)00352-4

Downstream raw materials:

(E)-(4S,7R,8S,9S,16S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-13-trityloxymethyl-oxacyclohexadec-13-ene-2,6-dione

(4S,7R,8S,9S,16S,E)-4,8-bis(tert-butyldimethylsilyloxy)-5,5,7,9-tetramethyl-16-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-13-(trityloxymethyl)oxacyclohexadec-13-ene-2,6-dione

26-fluoroepothilone B

Toluene-4-sulfonic acid (E)-(2S,9S,10S,11R,14S)-10,14-dihydroxy-9,11,13,13-tetramethyl-2-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-12,16-dioxo-oxacyclohexadec-4-en-5-ylmethyl ester

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