(1R,2S,3R,5S,δZ)-2-(tert-Butyldiphenylsilyloxy)methyl-5-hydroxy-3-tetrahydropyranyloxy-cyclopentanehept-δ-en-oic Acid Methyl Ester (Mixture of Diastereomers)

Base Information

• Chemical Name: (1R,2S,3R,5S,δZ)-2-(tert-Butyldiphenylsilyloxy)methyl-5-hydroxy-3-tetrahydropyranyloxy-cyclopentanehept-δ-en-oic Acid Methyl Ester (Mixture of Diastereomers)
• CAS No.: 172016-60-3
• Molecular Formula: C35H50O6Si
• Molecular Weight: 594.8534
• Mol file: 172016-60-3.mol

Synonyms:(1R,2S,3R,5S,δZ)-2-(tert-Butyldiphenylsilyloxy)methyl-5-hydroxy-3-tetrahydropyranyloxy-cyclopentanehept-δ-en-oic Acid Methyl Ester (Mixture of Diastereomers);[1R-[1α(Z),2β,3α,5α]]-7-[2-[[[(1,1-DiMethylethyl)diphenylsilyl]oxy]Methyl]-5-hydroxy-3-[(tetrahyd

Chemical Property of (1R,2S,3R,5S,δZ)-2-(tert-Butyldiphenylsilyloxy)methyl-5-hydroxy-3-tetrahydropyranyloxy-cyclopentanehept-δ-en-oic Acid Methyl Ester (Mixture of Diastereomers)

Chemical Property:

• PSA: 74.22000
• LogP: 5.76140
• Solubility.: Acetone, Chloroform, Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

97% ^*data from raw suppliers

(1R,2S,3R,5S,δZ)-2-(tert-Butyldiphenylsilyloxy)methyl-5-hydroxy-3-tetrahydropyranyloxy-cyclopentanehept-δ-en-oicAcidMethylEster(MixtureofDiastereomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate in the production of Limaprost.

Technology Process of (1R,2S,3R,5S,δZ)-2-(tert-Butyldiphenylsilyloxy)methyl-5-hydroxy-3-tetrahydropyranyloxy-cyclopentanehept-δ-en-oic Acid Methyl Ester (Mixture of Diastereomers)

There total 8 articles about (1R,2S,3R,5S,δZ)-2-(tert-Butyldiphenylsilyloxy)methyl-5-hydroxy-3-tetrahydropyranyloxy-cyclopentanehept-δ-en-oic Acid Methyl Ester (Mixture of Diastereomers) 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:

tert-butylchlorodiphenylsilane (58479-61-1) → methyl (±)-(5Z)-7-[(1R*,2S*,3R*,5S*)-2-{[tertbutyl(diphenyl)silyloxy]methyl}-5-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]hept-5-enoate (172016-60-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1H-imidazole / dichloromethane / 6 h

2: pyridinium p-toluenesulfonate / dichloromethane

3: diisobutylaluminium hydride / dichloromethane / -78 °C / Inert atmosphere

4: tetrahydrofuran / 1 h

5: diethyl ether

With 1H-imidazole; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; 4: |Wittig Olefination;

DOI:10.1134/S1070428015010017

Reference yield:

Corey (±)-lactone diol → methyl (±)-(5Z)-7-[(1R*,2S*,3R*,5S*)-2-{[tertbutyl(diphenyl)silyloxy]methyl}-5-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]hept-5-enoate (172016-60-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1H-imidazole / dichloromethane / 6 h

2: pyridinium p-toluenesulfonate / dichloromethane

3: diisobutylaluminium hydride / dichloromethane / -78 °C / Inert atmosphere

4: tetrahydrofuran / 1 h

5: diethyl ether

With 1H-imidazole; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; 4: |Wittig Olefination;

DOI:10.1134/S1070428015010017

Reference yield:

(1SR,5RS,6SR,7RS)-(+/-)-6-<(1,1-dimethylethyl)diphenylsilyloxymethyl>-7-hydroxy-2-oxabicyclo<3.3.0>octane-3-one (87858-95-5) → methyl (±)-(5Z)-7-[(1R*,2S*,3R*,5S*)-2-{[tertbutyl(diphenyl)silyloxy]methyl}-5-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]hept-5-enoate (172016-60-3)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridinium p-toluenesulfonate / dichloromethane

2: diisobutylaluminium hydride / dichloromethane / -78 °C / Inert atmosphere

3: tetrahydrofuran / 1 h

4: diethyl ether

With pyridinium p-toluenesulfonate; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; 3: |Wittig Olefination;

DOI:10.1134/S1070428015010017

upstream raw materials:

(4-carboxybutyl)triphenylphosphonium bromide

diazomethane

tert-butylchlorodiphenylsilane

(1SR,5RS,6SR,7RS)-(+/-)-6-<(1,1-dimethylethyl)diphenylsilyloxymethyl>-7-hydroxy-2-oxabicyclo<3.3.0>octane-3-one

Refernces