Cyclopentaneoctanoic acid, 3,5-bis(benzoyloxy)-2-(hydroxymethyl)-, methyl ester, (1R,2R,3S,5R)-

Base Information

Chemical Name:Cyclopentaneoctanoic acid, 3,5-bis(benzoyloxy)-2-(hydroxymethyl)-, methyl ester, (1R,2R,3S,5R)-
CAS No.:534584-86-6
Molecular Formula:C29H36O7
Molecular Weight:496.601
Hs Code.:

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of Cyclopentaneoctanoic acid, 3,5-bis(benzoyloxy)-2-(hydroxymethyl)-, methyl ester, (1R,2R,3S,5R)-

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Technology Process of Cyclopentaneoctanoic acid, 3,5-bis(benzoyloxy)-2-(hydroxymethyl)-, methyl ester, (1R,2R,3S,5R)-

There total 10 articles about Cyclopentaneoctanoic acid, 3,5-bis(benzoyloxy)-2-(hydroxymethyl)-, methyl ester, (1R,2R,3S,5R)- 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: 81.0%

: 534584-82-2
(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-[7-(methoxycarbonyl)heptyl]cyclopentane-1,4-diol

: 534584-86-6
(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(hydroxymethyl)-3-[7-(methoxycarbonyl)heptyl]cyclopentane-1,4-diol

Guidance literature:: With methanol; acetyl chloride; In diethyl ether; at 20 ℃; for 17h;
DOI:10.1021/jo035638i

Reference yield:

: 14273-91-7
methyl 6-iodohexanoate

: 534584-86-6
(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(hydroxymethyl)-3-[7-(methoxycarbonyl)heptyl]cyclopentane-1,4-diol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / K₂CO₃ / acetonitrile / 48 h / Heating

2.1: KHMDS / tetrahydrofuran; toluene / -80 - -40 °C

2.2: 70 percent / tetrahydrofuran; toluene / 2 h / -80 - 20 °C

3.1: 98 percent / hydrogen / Pd/C / methanol / 7 h / 3620.04 Torr

4.1: 77 percent / pyridine / 2 h / 20 °C

5.1: 81 percent / acetyl chloride; methanol / diethyl ether / 17 h / 20 °C

With pyridine; methanol; hydrogen; potassium hexamethylsilazane; potassium carbonate; acetyl chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; toluene; acetonitrile; 2.2: Wittig reaction;
DOI:10.1021/jo035638i

Reference yield:

: 4547-43-7
methyl 6-hydroxycaproate

: 534584-86-6
(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(hydroxymethyl)-3-[7-(methoxycarbonyl)heptyl]cyclopentane-1,4-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 61 percent / triphenylphosphine; iodine; imidazole / CH₂Cl₂ / -10 - 20 °C

2.1: 98 percent / K₂CO₃ / acetonitrile / 48 h / Heating

3.1: KHMDS / tetrahydrofuran; toluene / -80 - -40 °C

3.2: 70 percent / tetrahydrofuran; toluene / 2 h / -80 - 20 °C

4.1: 98 percent / hydrogen / Pd/C / methanol / 7 h / 3620.04 Torr

5.1: 77 percent / pyridine / 2 h / 20 °C

6.1: 81 percent / acetyl chloride; methanol / diethyl ether / 17 h / 20 °C

With pyridine; 1H-imidazole; methanol; hydrogen; iodine; potassium hexamethylsilazane; potassium carbonate; acetyl chloride; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; acetonitrile; 3.2: Wittig reaction;
DOI:10.1021/jo035638i