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

Base Information

Chemical Name:(1S,2S,3R,4R)-1,4-di-O-benzoyl-3-(4-methoxycarbonylbutyl)-2-[(3RS,E)-3-hydroxyoct-1-enyl]cyclopentane-1,4-diol
CAS No.:213777-28-7
Molecular Formula:C₃₃H₄₂O₇
Molecular Weight:550.692
Hs Code.:

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

There total 9 articles about (1S,2S,3R,4R)-1,4-di-O-benzoyl-3-(4-methoxycarbonylbutyl)-2-[(3RS,E)-3-hydroxyoct-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: 100.0%

: 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

: 213777-28-7
(1S,2S,3R,4R)-1,4-di-O-benzoyl-3-(4-methoxycarbonylbutyl)-2-[(3RS,E)-3-hydroxyoct-1-enyl]cyclopentane-1,4-diol

Guidance literature:: With L-Selectride; In tetrahydrofuran; at -78 ℃; for 0.333333h;
DOI:10.1016/S0040-4039(98)01290-8

Reference yield:

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

: 213777-28-7
(1S,2S,3R,4R)-1,4-di-O-benzoyl-3-(4-methoxycarbonylbutyl)-2-[(3RS,E)-3-hydroxyoct-1-enyl]cyclopentane-1,4-diol

Guidance literature:: Multi-step reaction with 10 steps

1: 83 percent / NaHMDS / tetrahydrofuran / -80 deg C; 20 deg C, 2 h

2: 95 percent / H₂ / 10percent Pd/C / 4 h

3: 91 percent / pyridine / 1 h / 20 °C

4: 87 percent / FeCl₃ / acetone / 3 h / Heating

5: m-CPBA / tetrahydrofuran / 20 °C

7: 83 percent / 3percent HCl / methanol / 20 °C

8: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -60 °C

9: NaH / tetrahydrofuran / 0.5 h / 20 °C

10: 100 percent / L-selectride / tetrahydrofuran / 0.33 h / -78 °C

With hydrogenchloride; oxalyl dichloride; hydrogen; sodium hexamethyldisilazane; iron(III) chloride; L-Selectride; sodium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; acetone;
DOI:10.1016/S0040-4039(98)01290-8

Reference yield:

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

: 213777-28-7
(1S,2S,3R,4R)-1,4-di-O-benzoyl-3-(4-methoxycarbonylbutyl)-2-[(3RS,E)-3-hydroxyoct-1-enyl]cyclopentane-1,4-diol

Guidance literature:: Multi-step reaction with 11 steps

1: 93 percent / DIBAL-H / toluene / 0.5 h / -80 °C

2: 83 percent / NaHMDS / tetrahydrofuran / -80 deg C; 20 deg C, 2 h

3: 95 percent / H₂ / 10percent Pd/C / 4 h

4: 91 percent / pyridine / 1 h / 20 °C

5: 87 percent / FeCl₃ / acetone / 3 h / Heating

6: m-CPBA / tetrahydrofuran / 20 °C

8: 83 percent / 3percent HCl / methanol / 20 °C

9: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -60 °C

10: NaH / tetrahydrofuran / 0.5 h / 20 °C

11: 100 percent / L-selectride / tetrahydrofuran / 0.33 h / -78 °C

With hydrogenchloride; oxalyl dichloride; hydrogen; sodium hexamethyldisilazane; iron(III) chloride; L-Selectride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; acetone; toluene;
DOI:10.1016/S0040-4039(98)01290-8