{3-[(3Z,8Z,16Z)-(5S,6S,7S,11S,12R,13R,14S,15S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,11,13,15-pentamethyl-nonadeca-3,8,16,18-tetraenyl]-phenyl}-carbamic acid tert-butyl ester

Base Information

Chemical Name:{3-[(3Z,8Z,16Z)-(5S,6S,7S,11S,12R,13R,14S,15S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,11,13,15-pentamethyl-nonadeca-3,8,16,18-tetraenyl]-phenyl}-carbamic acid tert-butyl ester
CAS No.:837383-66-1
Molecular Formula:C₄₇H₈₃NO₅Si₂
Molecular Weight:798.351
Hs Code.:

{3-[(3Z,8Z,16Z)-(5S,6S,7S,11S,12R,13R,14S,15S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,11,13,15-pentamethyl-nonadeca-3,8,16,18-tetraenyl]-phenyl}-carbamic acid tert-butyl ester

Synonyms:{3-[(3Z,8Z,16Z)-(5S,6S,7S,11S,12R,13R,14S,15S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,11,13,15-pentamethyl-nonadeca-3,8,16,18-tetraenyl]-phenyl}-carbamic acid tert-butyl ester

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Chemical Property of {3-[(3Z,8Z,16Z)-(5S,6S,7S,11S,12R,13R,14S,15S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,11,13,15-pentamethyl-nonadeca-3,8,16,18-tetraenyl]-phenyl}-carbamic acid tert-butyl ester

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Technology Process of {3-[(3Z,8Z,16Z)-(5S,6S,7S,11S,12R,13R,14S,15S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,11,13,15-pentamethyl-nonadeca-3,8,16,18-tetraenyl]-phenyl}-carbamic acid tert-butyl ester

There total 13 articles about {3-[(3Z,8Z,16Z)-(5S,6S,7S,11S,12R,13R,14S,15S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,11,13,15-pentamethyl-nonadeca-3,8,16,18-tetraenyl]-phenyl}-carbamic acid tert-butyl 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:

: 837383-35-4
[3-(3-oxo-propyl)-phenyl]-carbamic acid tert-butyl ester

: [(5Z,13Z)-(2R,3R,4S,8S,9R,10R,11S,12S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-2,4,8,10,12-pentamethyl-hexadeca-5,13,15-trienyl]-triphenyl-phosphonium; iodide

: 837383-66-1
{3-[(3Z,8Z,16Z)-(5S,6S,7S,11S,12R,13R,14S,15S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,11,13,15-pentamethyl-nonadeca-3,8,16,18-tetraenyl]-phenyl}-carbamic acid tert-butyl ester

Guidance literature:: [(5Z,13Z)-(2R,3R,4S,8S,9R,10R,11S,12S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-2,4,8,10,12-pentamethyl-hexadeca-5,13,15-trienyl]-triphenyl-phosphonium; iodide; With methyllithium; lithium bromide; In tetrahydrofuran; diethyl ether; at -78 - -20 ℃;

[3-(3-oxo-propyl)-phenyl]-carbamic acid tert-butyl ester; In tetrahydrofuran; diethyl ether; at -20 - -8 ℃; for 3h;

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/ol0476873

Reference yield:

: 837383-34-3
tert-butyl (3-(but-3-en-1-yl)phenyl)carbamate

: 837383-66-1
{3-[(3Z,8Z,16Z)-(5S,6S,7S,11S,12R,13R,14S,15S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,11,13,15-pentamethyl-nonadeca-3,8,16,18-tetraenyl]-phenyl}-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: O₃ / CH₂Cl₂ / 0.17 h / -78 °C

1.2: 66 percent / PPh₃ / CH₂Cl₂ / 1 h / 20 °C

2.1: MeLi/LiBr complex / tetrahydrofuran; diethyl ether / -78 - -20 °C

2.2: tetrahydrofuran; diethyl ether / 3 h / -20 - -8 °C

2.3: 12 mg / H₂O; DDQ / CH₂Cl₂ / 0 - 20 °C

With methyllithium; ozone; lithium bromide; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ol0476873

Reference yield:

: tert-Butyl-{(Z)-(1R,2S)-4-iodo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-but-3-enyloxy}-dimethyl-silane

: 837383-66-1
{3-[(3Z,8Z,16Z)-(5S,6S,7S,11S,12R,13R,14S,15S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,11,13,15-pentamethyl-nonadeca-3,8,16,18-tetraenyl]-phenyl}-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: ZnCl₂; t-BuLi / diethyl ether; pentane / 1 h / 20 °C

1.2: 60 percent / Pd(PPh₃)4 / diethyl ether; pentane / 20 °C

2.1: 80 percent / H₂O; DDQ / CH₂Cl₂ / 1 h / 0 °C

3.1: 87 percent / pyridine; DMAP / 18 h / Heating

4.1: 96 percent / DIBAL-H / CH₂Cl₂ / 4.5 h / 0 °C

5.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2.5 h / 0 °C

6.1: 79 percent / chlorocatecholborane; MeOH / CH₂Cl₂ / 0 °C

7.1: I₂; PPh₃; imidazole / diethyl ether; benzene / 0.5 h / 0 °C

8.1: 55 mg / i-Pr₂NEt / 8 h / 95 °C

9.1: MeLi/LiBr complex / tetrahydrofuran; diethyl ether / -78 - -20 °C

9.2: tetrahydrofuran; diethyl ether / 3 h / -20 - -8 °C

9.3: 12 mg / H₂O; DDQ / CH₂Cl₂ / 0 - 20 °C

With pyridine; 1H-imidazole; methanol; dmap; 2-chloro-1,3,2-benzodioxaborole; water; methyllithium; iodine; tert.-butyl lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium bromide; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; pentane; benzene;
DOI:10.1021/ol0476873