(5Z,8Z,11Z)-(14R,15R)-14-(tert-Butyl-diphenyl-silanyloxy)-15-hydroxy-icosa-5,8,11-trienoic acid methyl ester

Base Information

• Chemical Name: (5Z,8Z,11Z)-(14R,15R)-14-(tert-Butyl-diphenyl-silanyloxy)-15-hydroxy-icosa-5,8,11-trienoic acid methyl ester
• CAS No.: 98050-19-2
• Molecular Formula: C₃₇H₅₄O₄Si
• Molecular Weight: 590.919

Synonyms:(5Z,8Z,11Z)-(14R,15R)-14-(tert-Butyl-diphenyl-silanyloxy)-15-hydroxy-icosa-5,8,11-trienoic acid methyl ester

Chemical Property of (5Z,8Z,11Z)-(14R,15R)-14-(tert-Butyl-diphenyl-silanyloxy)-15-hydroxy-icosa-5,8,11-trienoic acid methyl ester

Chemical Property:

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Technology Process of (5Z,8Z,11Z)-(14R,15R)-14-(tert-Butyl-diphenyl-silanyloxy)-15-hydroxy-icosa-5,8,11-trienoic acid methyl ester

There total 1 articles about (5Z,8Z,11Z)-(14R,15R)-14-(tert-Butyl-diphenyl-silanyloxy)-15-hydroxy-icosa-5,8,11-trienoic acid methyl 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:

(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-pentyl-tetrahydro-furan-2-ol + <10-carbomethyoxynona-(Z,Z)-2,5-dien-1-yl>triphenylphosphonium bromide → (5Z,8Z,11Z)-(14R,15R)-14-(tert-Butyl-diphenyl-silanyloxy)-15-hydroxy-icosa-5,8,11-trienoic acid methyl ester (98050-19-2) + (5Z,8Z,11E)-(14R,15R)-14-(tert-Butyl-diphenyl-silanyloxy)-15-hydroxy-icosa-5,8,11-trienoic acid methyl ester

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; for 12h; Yield given; -78 to 23 deg C;

DOI:10.1021/ja00304a048

Reference yield:

p-toluenesulfonyl chloride (98-59-9) + (5Z,8Z,11Z)-(14R,15R)-14-(tert-Butyl-diphenyl-silanyloxy)-15-hydroxy-icosa-5,8,11-trienoic acid methyl ester (98050-19-2) → (5Z,8Z,11Z)-(14R,15R)-14-(tert-Butyl-diphenyl-silanyloxy)-15-(toluene-4-sulfonyloxy)-icosa-5,8,11-trienoic acid methyl ester

Guidance literature:

With pyridine; dmap; In dichloromethane; at 23 ℃; for 48h;

DOI:10.1021/ja00304a048

Reference yield:

(5Z,8Z,11Z)-(14R,15R)-14-(tert-Butyl-diphenyl-silanyloxy)-15-hydroxy-icosa-5,8,11-trienoic acid methyl ester (98050-19-2) → 14(R),15(S)-epoxyeicosatrienoic acid methyl ester (90080-09-4)

Guidance literature:

Multi-step reaction with 2 steps

1: py, DMAP / CH₂Cl₂ / 48 h / 23 °C

2: Bu₄NF / tetrahydrofuran / 24 h / 0 °C

With pyridine; dmap; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00304a048

Downstream raw materials:

14(R),15(S)-epoxyeicosatrienoic acid methyl ester

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