(E)-(5R,6S,7S,8S,9S,10S)-11-Benzyloxy-5-hydroxy-6,8,10-trimethyl-7,9-bis-triethylsilanyloxy-undec-2-enoic acid ethyl ester

Base Information

Chemical Name:(E)-(5R,6S,7S,8S,9S,10S)-11-Benzyloxy-5-hydroxy-6,8,10-trimethyl-7,9-bis-triethylsilanyloxy-undec-2-enoic acid ethyl ester
CAS No.:260433-45-2
Molecular Formula:C₃₅H₆₄O₆Si₂
Molecular Weight:637.061
Hs Code.:

Synonyms:(E)-(5R,6S,7S,8S,9S,10S)-11-Benzyloxy-5-hydroxy-6,8,10-trimethyl-7,9-bis-triethylsilanyloxy-undec-2-enoic acid ethyl ester

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Chemical Property of (E)-(5R,6S,7S,8S,9S,10S)-11-Benzyloxy-5-hydroxy-6,8,10-trimethyl-7,9-bis-triethylsilanyloxy-undec-2-enoic acid ethyl ester

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Technology Process of (E)-(5R,6S,7S,8S,9S,10S)-11-Benzyloxy-5-hydroxy-6,8,10-trimethyl-7,9-bis-triethylsilanyloxy-undec-2-enoic acid ethyl ester

There total 16 articles about (E)-(5R,6S,7S,8S,9S,10S)-11-Benzyloxy-5-hydroxy-6,8,10-trimethyl-7,9-bis-triethylsilanyloxy-undec-2-enoic acid ethyl 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:

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: 260433-44-1
(3R,4S,5S,6S,7S,8S)-9-Benzyloxy-3-hydroxy-4,6,8-trimethyl-5,7-bis-triethylsilanyloxy-nonanal

: 260433-45-2
(E)-(5R,6S,7S,8S,9S,10S)-11-Benzyloxy-5-hydroxy-6,8,10-trimethyl-7,9-bis-triethylsilanyloxy-undec-2-enoic acid ethyl ester

Guidance literature:: diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; at 0 ℃;

(3R,4S,5S,6S,7S,8S)-9-Benzyloxy-3-hydroxy-4,6,8-trimethyl-5,7-bis-triethylsilanyloxy-nonanal; In tetrahydrofuran; at 0 ℃;
DOI:10.1039/a908342a

Reference yield:

: 81520-04-9
(2S,3S,4S)-5-(benzyloxy)-2,3-epoxy-4-methyl-1-pentanol

: 260433-45-2
(E)-(5R,6S,7S,8S,9S,10S)-11-Benzyloxy-5-hydroxy-6,8,10-trimethyl-7,9-bis-triethylsilanyloxy-undec-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 16 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

2.1: NaH / tetrahydrofuran / 0 °C

2.2: tetrahydrofuran / 0 °C

3.1: 92 percent / H₂O / CH₂Cl₂ / -30 °C

4.1: imidazole; DMAP / CH₂Cl₂

5.1: DIBAL-H / tetrahydrofuran / 0 °C

6.1: MCPBA / CH₂Cl₂ / 0 °C

7.1: (COCl₂)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

8.1: NaH / tetrahydrofuran / 0 °C

8.2: tetrahydrofuran / 0 °C

9.1: Bu₄NF / tetrahydrofuran

10.1: 97 percent / H₂O / CH₂Cl₂ / -30 °C

11.1: imidazole; DMAP / CH₂Cl₂

12.1: DIBAL-H / tetrahydrofuran / 0 °C

13.1: MCPBA / CH₂Cl₂ / 0 °C

14.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

15.1: Na[PhSeB(OEt)3]; CH₃CO₂H / ethanol / 0 °C

16.1: NaH / tetrahydrofuran / 0 °C

16.2: tetrahydrofuran / 0 °C

With 1H-imidazole; dmap; oxalyl dichloride; (COCl₂)2; tetrabutyl ammonium fluoride; water; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; sodium phenylseleno(triethyl)borate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane; 1.1: Oxidation / 2.1: Metallation / 2.2: Condensation / 3.1: Methylation / 4.1: Etherification / 5.1: Reduction / 6.1: Epoxidation / 7.1: Oxidation / 8.1: Metallation / 8.2: Condensation / 9.1: Substitution / 10.1: Methylation / 11.1: Etherification / 12.1: Reduction / 13.1: Epoxidation / 14.1: Oxidation / 15.1: Reduction / 16.1: Metallation / 16.2: Condensation;
DOI:10.1039/a908342a

Reference yield:

: 994-30-9
triethylsilyl chloride

: 260433-45-2
(E)-(5R,6S,7S,8S,9S,10S)-11-Benzyloxy-5-hydroxy-6,8,10-trimethyl-7,9-bis-triethylsilanyloxy-undec-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: imidazole; DMAP / CH₂Cl₂

2.1: DIBAL-H / tetrahydrofuran / 0 °C

3.1: MCPBA / CH₂Cl₂ / 0 °C

4.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

5.1: Na[PhSeB(OEt)3]; CH₃CO₂H / ethanol / 0 °C

6.1: NaH / tetrahydrofuran / 0 °C

6.2: tetrahydrofuran / 0 °C

With 1H-imidazole; dmap; oxalyl dichloride; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; sodium phenylseleno(triethyl)borate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane; 1.1: Etherification / 2.1: Reduction / 3.1: Epoxidation / 4.1: Oxidation / 5.1: Reduction / 6.1: Metallation / 6.2: Condensation;
DOI:10.1039/a908342a