(1S,2S,3R,4R)-1,4-di-O-benzoyl-3-(4-methoxycarbonylbutyl)-2-[(E)-3-oxooct-1-enyl]cyclopentane-1,4-diol

Base Information

Chemical Name:(1S,2S,3R,4R)-1,4-di-O-benzoyl-3-(4-methoxycarbonylbutyl)-2-[(E)-3-oxooct-1-enyl]cyclopentane-1,4-diol
CAS No.:213777-27-6
Molecular Formula:C₃₃H₄₀O₇
Molecular Weight:548.676
Hs Code.:

Synonyms:(1S,2S,3R,4R)-1,4-di-O-benzoyl-3-(4-methoxycarbonylbutyl)-2-[(E)-3-oxooct-1-enyl]cyclopentane-1,4-diol

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Chemical Property of (1S,2S,3R,4R)-1,4-di-O-benzoyl-3-(4-methoxycarbonylbutyl)-2-[(E)-3-oxooct-1-enyl]cyclopentane-1,4-diol

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Technology Process of (1S,2S,3R,4R)-1,4-di-O-benzoyl-3-(4-methoxycarbonylbutyl)-2-[(E)-3-oxooct-1-enyl]cyclopentane-1,4-diol

There total 10 articles about (1S,2S,3R,4R)-1,4-di-O-benzoyl-3-(4-methoxycarbonylbutyl)-2-[(E)-3-oxooct-1-enyl]cyclopentane-1,4-diol 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:

: 213777-18-5
(1S,2S,3R,4R)-1,4-Bis(triethylsilyloxy)-3-(methoxycarbonylmethyl)-2-tert-butyldiphenylsilyloxymethylcyclopentane

: 213777-27-6
(1S,2S,3R,4R)-1,4-di-O-benzoyl-3-(4-methoxycarbonylbutyl)-2-[(E)-3-oxooct-1-enyl]cyclopentane-1,4-diol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 93 percent / DIBAL-H / toluene / 0.5 h / -78 °C

2.1: NaN(SiMe₃)2 / tetrahydrofuran / 2 h / -80 °C

2.2: 83 percent / tetrahydrofuran / 2 h / -80 - 20 °C

3.1: 95 percent / H₂ / Pd/C / 4 h / 2068.65 Torr

4.1: 91 percent / pyridine / 2 h / 20 °C

5.1: FeCl₃ / H₂O; acetone / 2 h / 20 °C

6.1: m-CPBA / tetrahydrofuran / 12 h / 20 °C

7.1: 53 mg / diethyl ether

8.1: 83 percent / acetyl chloride; methanol / diethyl ether / 20 °C

9.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -60 - 20 °C

10.1: NaH / tetrahydrofuran / 20 °C

10.2: 173 mg / tetrahydrofuran / 0.17 h / -10 °C

With pyridine; methanol; oxalyl dichloride; hydrogen; sodium hexamethyldisilazane; iron(III) chloride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; acetyl chloride; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; toluene; 2.2: Wittig reaction / 9.1: Swern oxidation / 10.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1002/1099-0690(200102)2001:4<809::AID-EJOC809>3.0.CO;2-6

Reference yield:

: 213777-19-6
(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(formylmethyl)-1,4-bis-O-(triethylsilyl)cyclopentane-1,4-diol

: 213777-27-6
(1S,2S,3R,4R)-1,4-di-O-benzoyl-3-(4-methoxycarbonylbutyl)-2-[(E)-3-oxooct-1-enyl]cyclopentane-1,4-diol

Guidance literature:: Multi-step reaction with 9 steps

1.1: NaN(SiMe₃)2 / tetrahydrofuran / 2 h / -80 °C

1.2: 83 percent / tetrahydrofuran / 2 h / -80 - 20 °C

2.1: 95 percent / H₂ / Pd/C / 4 h / 2068.65 Torr

3.1: 91 percent / pyridine / 2 h / 20 °C

4.1: FeCl₃ / H₂O; acetone / 2 h / 20 °C

5.1: m-CPBA / tetrahydrofuran / 12 h / 20 °C

6.1: 53 mg / diethyl ether

7.1: 83 percent / acetyl chloride; methanol / diethyl ether / 20 °C

8.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -60 - 20 °C

9.1: NaH / tetrahydrofuran / 20 °C

9.2: 173 mg / tetrahydrofuran / 0.17 h / -10 °C

With pyridine; methanol; oxalyl dichloride; hydrogen; sodium hexamethyldisilazane; iron(III) chloride; sodium hydride; dimethyl sulfoxide; triethylamine; acetyl chloride; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; 1.2: Wittig reaction / 8.1: Swern oxidation / 9.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1002/1099-0690(200102)2001:4<809::AID-EJOC809>3.0.CO;2-6

Reference yield:

: 213777-20-9
(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5,5-bis(isopropyloxy)pent-2-enyl]-1,4-di-O-(triethylsilyl)cyclopentane-1,4-diol

: 213777-27-6
(1S,2S,3R,4R)-1,4-di-O-benzoyl-3-(4-methoxycarbonylbutyl)-2-[(E)-3-oxooct-1-enyl]cyclopentane-1,4-diol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 95 percent / H₂ / Pd/C / 4 h / 2068.65 Torr

2.1: 91 percent / pyridine / 2 h / 20 °C

3.1: FeCl₃ / H₂O; acetone / 2 h / 20 °C

4.1: m-CPBA / tetrahydrofuran / 12 h / 20 °C

5.1: 53 mg / diethyl ether

6.1: 83 percent / acetyl chloride; methanol / diethyl ether / 20 °C

7.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -60 - 20 °C

8.1: NaH / tetrahydrofuran / 20 °C

8.2: 173 mg / tetrahydrofuran / 0.17 h / -10 °C

With pyridine; methanol; oxalyl dichloride; hydrogen; iron(III) chloride; sodium hydride; dimethyl sulfoxide; triethylamine; acetyl chloride; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; 7.1: Swern oxidation / 8.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1002/1099-0690(200102)2001:4<809::AID-EJOC809>3.0.CO;2-6