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

Base Information

• Chemical Name: methyl (5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11α-(tetrahydropyranyloxy)-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoate
• CAS No.: 101249-07-4
• Molecular Formula: C₄₈H₇₆O₆Si₂
• Molecular Weight: 805.299
• Mol file: 101249-07-4.mol

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

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

There total 1 articles about methyl (5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11α-(tetrahydropyranyloxy)-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: 100.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 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-(tetrahydropyranyloxy)-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoate (101249-07-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 1.5h; Ambient temperature;

DOI:10.1021/jo00359a055

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:

methyl (5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11α-(tetrahydropyranyloxy)-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoate (101249-07-4) → (5Z,13E)-9α-<(tert-butyldimethylsilyl)oxy>-11α-hydroxy-15-<(tert-butyldiphenylsilyl)oxy>prosta-5,13-dienoic acid (101249-09-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / acetonitrile / 336 h / 135 °C

2: 86 percent / 30percent aq.NaOH / 17 h / 0 °C

With sodium hydroxide; In acetonitrile;

DOI:10.1021/jo00359a055

upstream raw materials:

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

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

(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