(12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-12-trityloxymethyl-heptadeca-12,16-dien-5-one

Base Information

Chemical Name:(12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-12-trityloxymethyl-heptadeca-12,16-dien-5-one
CAS No.:201136-74-5
Molecular Formula:C₆₄H₁₀₁NO₆SSi₃
Molecular Weight:1096.83
Hs Code.:

(12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-12-trityloxymethyl-heptadeca-12,16-dien-5-one

Synonyms:(12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-12-trityloxymethyl-heptadeca-12,16-dien-5-one

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Chemical Property of (12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-12-trityloxymethyl-heptadeca-12,16-dien-5-one

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Technology Process of (12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-12-trityloxymethyl-heptadeca-12,16-dien-5-one

There total 12 articles about (12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-12-trityloxymethyl-heptadeca-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: 74.0%

: 201136-73-4
(12E,16E)-(3S,6R,7S,8S,15S)-1,3,7,15-Tetrakis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-12-trityloxymethyl-heptadeca-12,16-dien-5-one

: 201136-74-5
(12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-12-trityloxymethyl-heptadeca-12,16-dien-5-one

Guidance literature:: With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 0 - 25 ℃; for 4h;
DOI:10.1039/a705845d

Reference yield:

: 76-83-5
trityl chloride

: 201136-74-5
(12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-12-trityloxymethyl-heptadeca-12,16-dien-5-one

Guidance literature:: Multi-step reaction with 9 steps

1: 99 percent / 4-dimethylaminopyridine / dimethylformamide / 1 h / 70 °C

2: 1.) 9-BBN, 2.) aq. H₂O₂, aq. NaOH / 1.) THF, 0 deg C, 2 h, 2.) THF, 0 deg C, 0.5 h

3: 90 percent / I₂, PPh₃, imidazole / diethyl ether; acetonitrile / 0.5 h / 0 °C

4: diisopropylamine, n-BuLi / 1.) THF, hexane, 0 deg C, 14 h, 2.) THF, hexane, -100 to -20 deg C, 10 h

5: 91 percent / monoperoxyphthalic acid magnesium salt / methanol; H₂O; tetrahydrofuran / 1 h / 0 °C

6: 97 percent / DIBAL / toluene / 1 h / -78 °C

7: diisopropylamine, n-BuLi / 1.) THF, hexane, -78 deg C, 15 min, then -78 to -60 deg C, 1 h, 2.) THF, hexane, -78 deg C, 15 min

8: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

9: 74 percent / HF*pyridine / pyridine; tetrahydrofuran / 3 h / Ambient temperature

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; dihydrogen peroxide; iodine; diisobutylaluminium hydride; pyridine hydrogenfluoride; Monoperoxyphthalic acid, magnesium salt; diisopropylamine; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4020(98)00352-4

Reference yield:

: 193146-41-7
(2E,6E)(5S)-6-methyl-7-(2-methyl-(1,3-thiazol-4-yl))-2-prop-2-enyl-5-(1,1,2,2-tetramethyl-1-silapropoxy)hepta-2,6-dien-1-ol

: 201136-74-5
(12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-12-trityloxymethyl-heptadeca-12,16-dien-5-one

Guidance literature:: Multi-step reaction with 9 steps

1: 99 percent / 4-dimethylaminopyridine / dimethylformamide / 1 h / 70 °C

2: 1.) 9-BBN, 2.) aq. H₂O₂, aq. NaOH / 1.) THF, 0 deg C, 2 h, 2.) THF, 0 deg C, 0.5 h

3: 90 percent / I₂, PPh₃, imidazole / diethyl ether; acetonitrile / 0.5 h / 0 °C

4: diisopropylamine, n-BuLi / 1.) THF, hexane, 0 deg C, 14 h, 2.) THF, hexane, -100 to -20 deg C, 10 h

5: 91 percent / monoperoxyphthalic acid magnesium salt / methanol; H₂O; tetrahydrofuran / 1 h / 0 °C

6: 97 percent / DIBAL / toluene / 1 h / -78 °C

7: diisopropylamine, n-BuLi / 1.) THF, hexane, -78 deg C, 15 min, then -78 to -60 deg C, 1 h, 2.) THF, hexane, -78 deg C, 15 min

8: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

9: 74 percent / HF*pyridine / pyridine; tetrahydrofuran / 3 h / Ambient temperature

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; dihydrogen peroxide; iodine; diisobutylaluminium hydride; pyridine hydrogenfluoride; Monoperoxyphthalic acid, magnesium salt; diisopropylamine; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4020(98)00352-4