Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-benzyloxy-11,13-bis-(tert-butyl-dimethyl-silanyloxy)-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-tridec-3-enyl ester

Base Information

Chemical Name:Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-benzyloxy-11,13-bis-(tert-butyl-dimethyl-silanyloxy)-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-tridec-3-enyl ester
CAS No.:297131-79-4
Molecular Formula:C₄₅H₇₇NO₅SSi₂
Molecular Weight:800.347
Hs Code.:

Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-benzyloxy-11,13-bis-(tert-butyl-dimethyl-silanyloxy)-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-tridec-3-enyl ester

Synonyms:Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-benzyloxy-11,13-bis-(tert-butyl-dimethyl-silanyloxy)-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-tridec-3-enyl ester

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Chemical Property of Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-benzyloxy-11,13-bis-(tert-butyl-dimethyl-silanyloxy)-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-tridec-3-enyl ester

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Technology Process of Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-benzyloxy-11,13-bis-(tert-butyl-dimethyl-silanyloxy)-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-tridec-3-enyl ester

There total 25 articles about Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-benzyloxy-11,13-bis-(tert-butyl-dimethyl-silanyloxy)-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-tridec-3-enyl ester 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: 60.0%

: 186692-68-2
(1E,3S,5Z)-2-methyl-6-iodo-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-yl acetate

: 297131-72-7
{(1S,2S)-1-[(1R,2R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3,3-trimethyl-butyl]-2-methyl-pent-4-enyloxymethyl}-benzene

: 297131-79-4
Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-benzyloxy-11,13-bis-(tert-butyl-dimethyl-silanyloxy)-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-tridec-3-enyl ester

Guidance literature:: {(1S,2S)-1-[(1R,2R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3,3-trimethyl-butyl]-2-methyl-pent-4-enyloxymethyl}-benzene; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 20 ℃; for 4h;

(1E,3S,5Z)-2-methyl-6-iodo-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-yl acetate; With triphenyl-arsane; caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; water; for 1.5h;
DOI:10.1002/1099-0690(200105)2001:9<1701::AID-EJOC1701>3.0.CO;2-#

Reference yield:

: 14642-79-6
benzyloxy-trimethylsilane

: 297131-79-4
Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-benzyloxy-11,13-bis-(tert-butyl-dimethyl-silanyloxy)-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-tridec-3-enyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 16 h / -78 - -50 °C

2.1: BF₃*Et₂O / CH₂Cl₂ / 24 h / -30 °C

3.1: O₃; pyridine / methanol; CH₂Cl₂ / 0.5 h / -78 °C

3.2: 88 percent / dimethylsulfide / pyridine; methanol; CH₂Cl₂ / 16 h / 20 °C

4.1: TiCl₄ / CH₂Cl₂ / 0.75 h / -78 °C

5.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

6.1: 92 percent / tetrabutylammonium fluoride; acetic acid / tetrahydrofuran / 24 h / 20 °C

7.1: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

8.1: benzene / 4 h / Heating

9.1: 94 percent / trimethylsilyl chloride / tetrahydrofuran / 4 h / -78 °C

10.1: DIBAL-H / CH₂Cl₂ / 0.25 h / -78 °C

11.1: imidazole / dimethylformamide / 2 h / 0 °C

12.1: 90 percent / NaHMDS / tetrahydrofuran / 0.25 h / 0 °C

13.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C

13.2: 60 percent / Cs₂CO₃; AsPh₃ / PdCl₂(dppf) / H₂O; tetrahydrofuran / 1.5 h

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; 9-borabicyclo[3.3.1]nonane dimer; chloro-trimethyl-silane; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; titanium tetrachloride; diisobutylaluminium hydride; ozone; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 7.1: Swern oxidation / 12.1: Wittig olefination;
DOI:10.1002/1099-0690(200105)2001:9<1701::AID-EJOC1701>3.0.CO;2-#

Reference yield:

: 186692-81-9
(1E,3S,5Z)-2-methyl-6-iodo-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-ol

: 297131-79-4
Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-benzyloxy-11,13-bis-(tert-butyl-dimethyl-silanyloxy)-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-tridec-3-enyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 95 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h / 0 °C

2.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C

2.2: 60 percent / Cs₂CO₃; AsPh₃ / PdCl₂(dppf) / H₂O; tetrahydrofuran / 1.5 h

With dmap; 9-borabicyclo[3.3.1]nonane dimer; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1002/1099-0690(200105)2001:9<1701::AID-EJOC1701>3.0.CO;2-#