phenyl-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-2,4,8,10-tetramethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester

Base Information

• Chemical Name: phenyl-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-2,4,8,10-tetramethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester
• CAS No.: 835929-56-1
• Molecular Formula: C₆₂H₁₁₃NO₈Si₄
• Molecular Weight: 1112.92

Synonyms:phenyl-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-2,4,8,10-tetramethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester

Chemical Property of phenyl-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-2,4,8,10-tetramethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of phenyl-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-2,4,8,10-tetramethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester

There total 12 articles about phenyl-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-2,4,8,10-tetramethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl 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: 87.0%

(3R,4S,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-[(3Z,8Z,16Z)-(2S,5S,6R,7S,11S,12R,13R,14S,15S)-2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,11,13,15-pentamethyl-nonadeca-3,8,16,18-tetraenyl]-tetrahydro-pyran-2-one (835929-26-5) + phenyl isocyanate (103-71-9) → phenyl-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-2,4,8,10-tetramethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester (835929-56-1)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/ol047686a

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 → phenyl-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-2,4,8,10-tetramethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester (835929-56-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: ZnCl₂; t-BuLi / diethyl ether / -78 - 20 °C

1.2: 60 percent / Pd(PPh₃)4 / diethyl ether

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

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

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

5.1: t-BuLi; Ti(O-i-Pr)4 / tetrahydrofuran; pentane / 0.5 h / -78 °C

5.2: tetrahydrofuran; pentane / -78 - 0 °C

5.3: MeI / tetrahydrofuran; pentane / 16 h / 20 °C

6.1: chlorocatecholborane; MeOH / CH₂Cl₂ / 0 °C

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

8.1: 55 mg / i-Pr₂NEt / 8 h / 95 °C

9.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.75 h / -20 - 0 °C

9.2: 35 percent / tetrahydrofuran / 3.25 h / -24 - -8 °C

10.1: 95 percent / H₂O; DDQ / CH₂Cl₂ / 0.25 h / 0 - 20 °C

11.1: 87 percent / pyridine / CH₂Cl₂ / 16 h / 20 °C

With pyridine; titanium(IV) isopropylate; methanol; dmap; 2-chloro-1,3,2-benzodioxaborole; water; iodine; tert.-butyl lithium; sodium hexamethyldisilazane; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; pentane;

DOI:10.1021/ol047686a

Reference yield:

(Z)-(2S,3R,4S,8S,9R,10R)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,8-trimethyl-undec-5-en-1-ol (835929-77-6) → phenyl-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-2,4,8,10-tetramethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester (835929-56-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 87 percent / DMAP; pyridine / 18 h / Heating

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

3.1: t-BuLi; Ti(O-i-Pr)4 / tetrahydrofuran; pentane / 0.5 h / -78 °C

3.2: tetrahydrofuran; pentane / -78 - 0 °C

3.3: MeI / tetrahydrofuran; pentane / 16 h / 20 °C

4.1: chlorocatecholborane; MeOH / CH₂Cl₂ / 0 °C

5.1: I₂; PPh₃ / diethyl ether / 0.5 h / 0 °C

6.1: 55 mg / i-Pr₂NEt / 8 h / 95 °C

7.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.75 h / -20 - 0 °C

7.2: 35 percent / tetrahydrofuran / 3.25 h / -24 - -8 °C

8.1: 95 percent / H₂O; DDQ / CH₂Cl₂ / 0.25 h / 0 - 20 °C

9.1: 87 percent / pyridine / CH₂Cl₂ / 16 h / 20 °C

With pyridine; titanium(IV) isopropylate; methanol; dmap; 2-chloro-1,3,2-benzodioxaborole; water; iodine; tert.-butyl lithium; sodium hexamethyldisilazane; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; pentane;

DOI:10.1021/ol047686a

upstream raw materials:

(3R,4S,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-[(3Z,8Z,16Z)-(2S,5S,6R,7S,11S,12R,13R,14S,15S)-2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,11,13,15-pentamethyl-nonadeca-3,8,16,18-tetraenyl]-tetrahydro-pyran-2-one

phenyl isocyanate

(Z)-(2S,3R,4S,8S,9R,10R)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,8-trimethyl-undec-5-en-1-ol

(5Z,13Z)-(2S,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-trien-1-ol

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