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

Base Information

• Chemical Name: (5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11-oxo-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoic acid
• CAS No.: 101249-10-9
• Molecular Formula: C₄₂H₆₄O₅Si₂
• Molecular Weight: 705.138
• Mol file: 101249-10-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 5 articles about (5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11-oxo-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoic 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: 87.0%

(5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11α-hydroxy-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoic acid (101249-09-6) → (5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11-oxo-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoic acid (101249-10-9)

Guidance literature:

With sodium acetate; pyridinium chlorochromate; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jo00359a055

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11-oxo-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoic acid (101249-10-9)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 86 percent / 30percent aq.NaOH / 17 h / 0 °C

4: 87 percent / pyridinium chlorochromate, NaOAc / CH₂Cl₂ / 1 h / Ambient temperature

With 1H-imidazole; sodium hydroxide; sodium acetate; pyridinium chlorochromate; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00359a055

Reference yield:

methyl (5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11α-hydroxy-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoate (101249-08-5) → (5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11-oxo-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoic acid (101249-10-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / 30percent aq.NaOH / 17 h / 0 °C

2: 87 percent / pyridinium chlorochromate, NaOAc / CH₂Cl₂ / 1 h / Ambient temperature

With sodium hydroxide; sodium acetate; pyridinium chlorochromate; In dichloromethane;

DOI:10.1021/jo00359a055

upstream raw materials:

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

tert-butyldimethylsilyl chloride

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

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