5-Heptenoic acid, 7-[(3R)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-oxo-1-cyclopenten-1-yl ]-, methyl ester, (5Z)-

Base Information

• Chemical Name: 5-Heptenoic acid, 7-[(3R)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-oxo-1-cyclopenten-1-yl ]-, methyl ester, (5Z)-
• CAS No.: 82542-42-5
• Molecular Formula: C19H32O4Si
• Molecular Weight: 352.546
• Mol file: 82542-42-5.mol

Synonyms:(R,Z)-Methyl 7-(3-((tert-butyldimethylsilyl)oxy)-5-oxocyclopent-1-en-1-yl)hept-5-enoate;4-(R)-t-butyldimethylsilyloxy-2-(6-carbomethoxy-2-hexenyl)-2-cyclopentenone;(Z)-7-[(R)-3-(tert-Butyldimethylsilanyloxy)-5-oxo-cyclopent-1-enyl]hept-5-enoic acid methyl ester;Methyl (Z)-7-{(3R)-3-[(tert-Butyldimethylsilyl)oxy]-5-oxo-1-cyclopentenyl}-5-heptenoate;

Chemical Property of 5-Heptenoic acid, 7-[(3R)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-oxo-1-cyclopenten-1-yl ]-, methyl ester, (5Z)-

Chemical Property:

• PSA: 52.60000
• LogP: 4.56560
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R,Z)-Methyl 7-(3-((tert-butyldimethylsilyl)-oxy)-5-oxocyclopent-1-en-1-yl)hept-5-enoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-Heptenoic acid, 7-[(3R)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-oxo-1-cyclopenten-1-yl ]-, methyl ester, (5Z)-

There total 26 articles about 5-Heptenoic acid, 7-[(3R)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-oxo-1-cyclopenten-1-yl ]-, methyl ester, (5Z)- 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: 89.0%

5-Benzenesulfinyl-7-[3-(tert-butyl-dimethyl-silanyloxy)-5-oxo-cyclopent-1-enyl]-hepta-5,6-dienoic acid methyl ester (121221-98-5) → Methyl (Z)-7-<(3R)-3-<(tert-Butyldimethylsilyl)oxy>-5-oxo-1-cyclopentenyl>-5-heptenoate (82542-42-5,132619-70-6)

Guidance literature:

With hydrogen; Lindlar's catalyst; at 21 ℃; for 15h;

DOI:10.1016/S0040-4039(01)80309-9

Reference yield:

methyl 7-(tetrahydro-2'H-pyran-2'-yloxy)hept-5-ynoate (50781-90-3) → Methyl (Z)-7-<(3R)-3-<(tert-Butyldimethylsilyl)oxy>-5-oxo-1-cyclopentenyl>-5-heptenoate (82542-42-5,132619-70-6)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Lindlar's catalyst / ethyl acetate

2: camphorsulfonic acid / methanol

3: CBr₄, triphenylphosphine / acetonitrile

4: NaI / acetone

With carbon tetrabromide; camphor-10-sulfonic acid; hydrogen; triphenylphosphine; sodium iodide; Lindlar's catalyst; In methanol; ethyl acetate; acetone; acetonitrile;

DOI:10.1021/jo00037a035

Reference yield:

(S)-1-[(R)-oxiran-2-yl]prop-2-enol (100017-22-9) → Methyl (Z)-7-<(3R)-3-<(tert-Butyldimethylsilyl)oxy>-5-oxo-1-cyclopentenyl>-5-heptenoate (82542-42-5,132619-70-6)

Guidance literature:

Multi-step reaction with 12 steps

1: NaH / tetrahydrofuran / 2 h / 0 °C

2: AcOH / methanol / 6 h / 40 °C

3: imidazole / dimethylformamide / 10 h / Ambient temperature

4: diisobutylaluminum hydride (Dibal) / hexane; diethyl ether / 0.5 h / -20 °C

5: NH₂OH*HCl, pyridine / CH₂Cl₂ / 4 h / Ambient temperature

6: NaOCl / CH₂Cl₂ / 4 h / Ambient temperature

7: H₂, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H₂O / 4 h / 760 Torr / Ambient temperature

8: CH₃SO₂Cl, Et₃N / CH₂Cl₂ / 0.67 h / 0 °C

9: 1.) CuCN / 2.) THF, from -78 deg C to 0 deg C, 1 h

10: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether

11: CrO₃, H⁺

With pyridine; 1H-imidazole; chromium(VI) oxide; sodium hypochlorite; hydroxylamine hydrochloride; hydrogen; boric acid; pyridinium p-toluenesulfonate; hydrogen cation; sodium hydride; diisobutylaluminium hydride; acetic acid; methanesulfonyl chloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00258a051

upstream raw materials:

diazomethane

(Z)-7-[(R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-oxo-cyclopent-1-enyl]-hept-5-enoic acid

methyl (5Z)-7-iodo-5-heptenoate

(4R)-4-<(tert-butyldimethylsilyl)oxy>-2-(phenylseleno)-2-cyclopenten-1-one

Downstream raw materials:

Methyl (Z)-7-<(3R)-3-Hydroxy-5-oxo-1-cyclopentenyl>-5-heptenoate

(Z)-7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-4-(tert-butyl-dimethyl-silanyloxy)-4-(1-propyl-cyclohexyl)-but-1-enyl]-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester

(Z)-7-[(1R,2R,3R)-2-[(E)-4-(1-Benzyl-cyclobutyl)-4-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-oxo-cyclopentyl]-hept-5-enoic acid methyl ester

(Z)-7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-4-(tert-butyl-dimethyl-silanyloxy)-4-(1-cyclohexylmethyl-cyclobutyl)-but-1-enyl]-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester

Refernces

• 1、 Kusuda, Shinya,Watanabe, Yoshihiko,Ueno, Yoshio,Toru, Takeshi. "A Novel Vinyl Anion Equivalent. An Extremely Short Synthesis of 2-Substituted 2-Cycloalkenones and Prostaglandin Key Intermediates via Destannylselenenylation". . p. 3145 - 3152. Retrieved 2007/10/02.
• 2、 Levin, Jeremy I.. "A NOVEL AND EFFICIENT ROUTE TO PROSTANOID INTERMEDIATES". . p. 13 - 14. Retrieved 2007/10/02.