(-)-11α,15α-bis<(tert-butyldimethylsilyl)oxy>-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-4,15,13(t)-trienoic acid methyl ester

Base Information

• Chemical Name: (-)-11α,15α-bis<(tert-butyldimethylsilyl)oxy>-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-4,15,13(t)-trienoic acid methyl ester
• CAS No.: 157543-66-3
• Molecular Formula: C₃₅H₅₆O₆Si₂
• Molecular Weight: 628.997
• Mol file: 157543-66-3.mol

Synonyms:(-)-11α,15α-bis<(tert-butyldimethylsilyl)oxy>-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-4,15,13(t)-trienoic acid methyl ester

Chemical Property of (-)-11α,15α-bis<(tert-butyldimethylsilyl)oxy>-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-4,15,13(t)-trienoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-11α,15α-bis<(tert-butyldimethylsilyl)oxy>-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-4,15,13(t)-trienoic acid methyl ester

There total 6 articles about (-)-11α,15α-bis<(tert-butyldimethylsilyl)oxy>-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-4,15,13(t)-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:

(3S,4R)-3-(Methoxymethyloxy)-2-methylidene-4-(tert-butyldimethylsiloxy)cyclopentanone (117253-98-2) → (-)-11α,15α-bis<(tert-butyldimethylsilyl)oxy>-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-4,15,13(t)-trienoic acid methyl ester (157543-66-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / BF₃*OEt₂ / tetrahydrofuran / 2 h / -78 - 0 °C

2: 1.) pyridinium toluene-p-sulfonate, 2.) CrO₃, acid

4: 1.) n-Bu₃SnH, AIBN

With chromium(VI) oxide; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; In tetrahydrofuran;

DOI:10.1039/c39940001251

Reference yield:

7-[(R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-oxo-cyclopent-1-enyl]-hepta-4,5-dienoic acid → (-)-11α,15α-bis<(tert-butyldimethylsilyl)oxy>-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-4,15,13(t)-trienoic acid methyl ester (157543-66-3)

Guidance literature:

Multi-step reaction with 2 steps

2: 1.) n-Bu₃SnH, AIBN

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride;

DOI:10.1039/c39940001251

Reference yield:

(R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[7-(1-ethoxy-ethoxy)-hepta-2,3-dienyl]-cyclopent-2-enone → (-)-11α,15α-bis<(tert-butyldimethylsilyl)oxy>-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-4,15,13(t)-trienoic acid methyl ester (157543-66-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) pyridinium toluene-p-sulfonate, 2.) CrO₃, acid

3: 1.) n-Bu₃SnH, AIBN

With chromium(VI) oxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate;

DOI:10.1039/c39940001251

upstream raw materials:

(R)-3-<(tert-butyldimethylsilyl)oxy>-4-phenoxy-1-butyne

(3S,4R)-3-(Methoxymethyloxy)-2-methylidene-4-(tert-butyldimethylsiloxy)cyclopentanone

Downstream raw materials:

(dl)-9-keto-11α,15α-dihydroxy-16-phenoxy-17,18,19,20-tetranorprosta-4,5,13-trans-trienoic acid methyl ester

Refernces

• 1、 Gooding, Owen W.,Beard, Colin C.,Cooper, Gary F.,Jackson, David Y.. "Triply Convergent Synthesis of 15-(Phenoxymethyl) and 4,5-Allenyl Prostaglandins. Preparation of an Individual Isomer of Enprostil". . p. 3681 - 3686. Retrieved 2007/10/02.