methyl (5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11α-hydroxy-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoate

Base Information

• Chemical Name: methyl (5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11α-hydroxy-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoate
• CAS No.: 101249-08-5
• Molecular Formula: C₄₃H₆₈O₅Si₂
• Molecular Weight: 721.181
• Mol file: 101249-08-5.mol

Synonyms:methyl (5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11α-hydroxy-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoate

Chemical Property of methyl (5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11α-hydroxy-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11α-hydroxy-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoate

There total 3 articles about methyl (5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11α-hydroxy-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoate 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: 76.0%

methyl (5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11α-(tetrahydropyranyloxy)-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoate (101249-07-4) → methyl (5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11α-hydroxy-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoate (101249-08-5)

Guidance literature:

In acetonitrile; at 135 ℃; for 336h;

DOI:10.1021/jo00359a055

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → methyl (5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11α-hydroxy-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoate (101249-08-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / imidazole / dimethylformamide / 1.5 h / Ambient temperature

2: 76 percent / acetonitrile / 336 h / 135 °C

With 1H-imidazole; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00359a055

Reference yield:

methyl (5Z,13E)-9α-hydroxy-11α-(tetrahydropyranyloxy)-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoate (101249-06-3) → methyl (5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11α-hydroxy-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoate (101249-08-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / imidazole / dimethylformamide / 1.5 h / Ambient temperature

2: 76 percent / acetonitrile / 336 h / 135 °C

With 1H-imidazole; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00359a055

upstream raw materials:

methyl (5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11α-(tetrahydropyranyloxy)-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoate

tert-butyldimethylsilyl chloride

methyl (5Z,13E)-9α-hydroxy-11α-(tetrahydropyranyloxy)-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoate

Downstream raw materials:

(5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11α-hydroxy-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoic acid

(5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11-oxo-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoic acid