3,7-dithia-16-phenyl-ω-tetranorPGE₁ methyl ester 11,15-bis(tert-butyldimethylsilyl ether)

Base Information

• Chemical Name: 3,7-dithia-16-phenyl-ω-tetranorPGE₁ methyl ester 11,15-bis(tert-butyldimethylsilyl ether)
• CAS No.: 433213-39-9
• Molecular Formula: C₃₃H₅₆O₅S₂Si₂
• Molecular Weight: 653.108

Synonyms:3,7-dithia-16-phenyl-ω-tetranorPGE₁ methyl ester 11,15-bis(tert-butyldimethylsilyl ether)

Chemical Property of 3,7-dithia-16-phenyl-ω-tetranorPGE₁ methyl ester 11,15-bis(tert-butyldimethylsilyl ether)

Chemical Property:

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Technology Process of 3,7-dithia-16-phenyl-ω-tetranorPGE₁ methyl ester 11,15-bis(tert-butyldimethylsilyl ether)

There total 2 articles about 3,7-dithia-16-phenyl-ω-tetranorPGE₁ methyl ester 11,15-bis(tert-butyldimethylsilyl ether) 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: 65.0%

((E)-(S)-1-Benzyl-3-iodo-allyloxy)-tert-butyl-dimethyl-silane + 2-(6-carbomethoxy-1,5-dithiahexyl)-4-(R)-tert-butyldimethylsilyloxy-2-cyclopentenone (210819-03-7) → 3,7-dithia-16-phenyl-ω-tetranorPGE1 methyl ester 11,15-bis(tert-butyldimethylsilyl ether) (433213-39-9)

Guidance literature:

((E)-(S)-1-Benzyl-3-iodo-allyloxy)-tert-butyl-dimethyl-silane; With tert.-butyl lithium; In diethyl ether; pentane; at -70 ℃; for 1h;

2-(6-carbomethoxy-1,5-dithiahexyl)-4-(R)-tert-butyldimethylsilyloxy-2-cyclopentenone; With thien-2-yl(cyano)copper lithium; In tetrahydrofuran; diethyl ether; pentane; at -70 - -20 ℃; for 1h;

DOI:10.1016/S0968-0896(01)00351-0

Reference yield:

6-mercapto-3-thiahexanoic acid methyl ester (164214-15-7) → 3,7-dithia-16-phenyl-ω-tetranorPGE1 methyl ester 11,15-bis(tert-butyldimethylsilyl ether) (433213-39-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 83 percent / alumina / CH₂Cl₂ / 12 h / 20 °C

2.1: t-BuLi / diethyl ether; pentane / 1 h / -70 °C

2.2: 65 percent / lithium 2-thienylcyanocuprate / diethyl ether; pentane; tetrahydrofuran / 1 h / -70 - -20 °C

With aluminum oxide; tert.-butyl lithium; In diethyl ether; dichloromethane; pentane;

DOI:10.1016/S0968-0896(01)00351-0

Reference yield: 79.0%

3,7-dithia-16-phenyl-ω-tetranorPGE1 methyl ester 11,15-bis(tert-butyldimethylsilyl ether) (433213-39-9) → 3,7-dithia-16-phenyl-ω-tetranorprostaglandin E1 methyl ester (210818-97-6)

Guidance literature:

With (HF)n*pyridine; In pyridine; acetonitrile; at 20 ℃;

DOI:10.1016/S0968-0896(01)00351-0

upstream raw materials:

2-(6-carbomethoxy-1,5-dithiahexyl)-4-(R)-tert-butyldimethylsilyloxy-2-cyclopentenone

6-mercapto-3-thiahexanoic acid methyl ester

Downstream raw materials:

3,7-dithia-16-phenyl-ω-tetranorprostaglandin E₁ methyl ester

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