(13E)-(+/-)-9α-benzyloxy-15-(t-butyldimethylsilyloxy)-11α-hydroxyprosta-13-enoic acid

Base Information

• Chemical Name: (13E)-(+/-)-9α-benzyloxy-15-(t-butyldimethylsilyloxy)-11α-hydroxyprosta-13-enoic acid
• CAS No.: 77426-11-0
• Molecular Formula: C₃₃H₅₆O₅Si
• Molecular Weight: 560.89
• Mol file: 77426-11-0.mol

Synonyms:

Chemical Property of (13E)-(+/-)-9α-benzyloxy-15-(t-butyldimethylsilyloxy)-11α-hydroxyprosta-13-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (13E)-(+/-)-9α-benzyloxy-15-(t-butyldimethylsilyloxy)-11α-hydroxyprosta-13-enoic acid

There total 8 articles about (13E)-(+/-)-9α-benzyloxy-15-(t-butyldimethylsilyloxy)-11α-hydroxyprosta-13-enoic acid 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:

(5Z,13E)-(+/-)-9α-benzyloxy-15-(t-butyldimethylsilyloxy)-11α-hydroxyprosta-5,13-dienoic acid (77426-06-3,77426-23-4) → (13E)-(+/-)-9α-benzyloxy-15-(t-butyldimethylsilyloxy)-11α-hydroxyprosta-13-enoic acid (77426-11-0,77426-25-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at -23 ℃; for 8h;

DOI:10.1039/P19810000646

Reference yield:

(4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → (13E)-(+/-)-9α-benzyloxy-15-(t-butyldimethylsilyloxy)-11α-hydroxyprosta-13-enoic acid (77426-11-0,77426-25-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) potassium t-butoxide / 1.) THF, 15 min, 2.) 30 min

2: H₂ / 5percent Pd-C / ethanol / 8 h / -23 °C

With potassium tert-butylate; hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1039/P19810000646

Reference yield:

3-endo-benzyloxytricyclo<3.2.0.02,7>heptan-6-one (64767-30-2,68974-44-7,135500-82-2) → (13E)-(+/-)-9α-benzyloxy-15-(t-butyldimethylsilyloxy)-11α-hydroxyprosta-13-enoic acid (77426-11-0,77426-25-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) n-BuLi, 2.) pent-1-ynylcopper

2: 1.) 40percent peracetic acid, sodium acetate, 2.) glacial acetic acid, H₂O, sodium acetate / 1.) CH₂Cl₂, 20 deg C, 16 h, 2.) 20 deg C, 8 d

3: 2.) di-isobutylaluminium hydride

4: 1.) potassium t-butoxide / 1.) THF, 15 min, 2.) 30 min

5: H₂ / 5percent Pd-C / ethanol / 8 h / -23 °C

With 1-pentynyl copper; peracetic acid; n-butyllithium; diisobutylaluminum hydride; potassium tert-butylate; water; hydrogen; sodium acetate; acetic acid; palladium on activated charcoal; In ethanol;

DOI:10.1039/P19810000646

upstream raw materials:

(5Z,13E)-(+/-)-9α-benzyloxy-15-(t-butyldimethylsilyloxy)-11α-hydroxyprosta-5,13-dienoic acid

(4-carboxybutyl)triphenylphosphonium bromide

3-endo-benzyloxytricyclo<3.2.0.0^2,7>heptan-6-one

3-endo-benzyloxy-2-exo-bromobicyclo<3.2.0>heptan-6-one

Downstream raw materials:

methyl (13E,15S^*)-(+/-)-9α-benzyloxy-15-hydroxy-11-oxoprosta-13-enoate

methyl 15-epi-(13E,15S^*)-(+/-)-9α-benzyloxy-15-hydroxy-11-oxoprosta-13-enoate