(2α,6β,10α,11α)-12-benzylthio-5,5-ethylenedioxy-11-methoxycarbonyl-15-oxatetracyclo<10.2.1.0^3,12.0^7,11>pentadeca-13-en-9-one

Base Information

• Chemical Name: (2α,6β,10α,11α)-12-benzylthio-5,5-ethylenedioxy-11-methoxycarbonyl-15-oxatetracyclo<10.2.1.0^3,12.0^7,11>pentadeca-13-en-9-one
• CAS No.: 135186-51-5
• Molecular Formula: C₂₅H₂₈O₆S
• Molecular Weight: 456.56

Synonyms:(2α,6β,10α,11α)-12-benzylthio-5,5-ethylenedioxy-11-methoxycarbonyl-15-oxatetracyclo<10.2.1.0^3,12.0^7,11>pentadeca-13-en-9-one

Chemical Property of (2α,6β,10α,11α)-12-benzylthio-5,5-ethylenedioxy-11-methoxycarbonyl-15-oxatetracyclo<10.2.1.0^3,12.0^7,11>pentadeca-13-en-9-one

Chemical Property:

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Technology Process of (2α,6β,10α,11α)-12-benzylthio-5,5-ethylenedioxy-11-methoxycarbonyl-15-oxatetracyclo<10.2.1.0^3,12.0^7,11>pentadeca-13-en-9-one

There total 12 articles about (2α,6β,10α,11α)-12-benzylthio-5,5-ethylenedioxy-11-methoxycarbonyl-15-oxatetracyclo<10.2.1.0^3,12.0^7,11>pentadeca-13-en-9-one 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: 68.0%

(2α,3β)-1,1-ethylenedioxy-3-(5-benzylthio-2-furyl)-2-<(4Z)-3-oxo-5-methoxycarbonylpent-4-enyl>cyclopentane (135186-47-9) → (2α,6β,10α,11α)-12-benzylthio-5,5-ethylenedioxy-11-methoxycarbonyl-15-oxatetracyclo<10.2.1.03,12.07,11>pentadeca-13-en-9-one (135186-51-5)

Guidance literature:

In dichloromethane; at 20 ℃; for 13h; under 14251100 Torr;

DOI:10.1039/c39910000527

Reference yield:

(2α,3β)-1,1-ethylenedioxy-3-(5-benzylthio-2-furyl)-2-(3-oxopropyl)cyclopentane (135186-48-0) → (2α,6β,10α,11α)-12-benzylthio-5,5-ethylenedioxy-11-methoxycarbonyl-15-oxatetracyclo<10.2.1.03,12.07,11>pentadeca-13-en-9-one (135186-51-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, -78 deg C, 40 min

2: H₂ / 5 percent Pd/BaSO₄ / ethyl acetate / 3 h / Ambient temperature

3: 73 percent / Swern oxidation conditions

4: 68 percent / CH₂Cl₂ / 15 h / 20 °C / 14251100 Torr

With n-butyllithium; hydrogen; Pd-BaSO₄; In dichloromethane; ethyl acetate;

Reference yield:

(2α,3β)-1,1-ethylenedioxy-3-(5-benzylthio-2-furyl)-2-(3-hydroxy-5-methoxycarbonylpent-4-ynyl)cyclopentane (135186-57-1,135269-06-6) → (2α,6β,10α,11α)-12-benzylthio-5,5-ethylenedioxy-11-methoxycarbonyl-15-oxatetracyclo<10.2.1.03,12.07,11>pentadeca-13-en-9-one (135186-51-5)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / 5 percent Pd/BaSO₄ / ethyl acetate / 3 h / Ambient temperature

2: 73 percent / Swern oxidation conditions

3: 68 percent / CH₂Cl₂ / 15 h / 20 °C / 14251100 Torr

With hydrogen; Pd-BaSO₄; In dichloromethane; ethyl acetate;

upstream raw materials:

(2α,3β)-1,1-ethylenedioxy-3-(5-benzylthio-2-furyl)-2-<(4Z)-3-oxo-5-methoxycarbonylpent-4-enyl>cyclopentane

2-(benzylthio)furan

6-bromo-1,4-dioxa-spiro[4.4]non-6-ene

2-allyl-2-cyclopenten-1-one

Downstream raw materials:

C₂₅H₂₈O₆S

(2α,6β,10α,11α)-12-benzylthio-5,5-ethylenedioxy-11-methoxycarbonyl-15-oxatetracyclo<10.2.1.0^3,12.0^7,11>pentadecan-9-one

(2α,6β,10β,11α)-12-benzylthio-5,5-ethylenedioxy-11-methoxycarbonyl-15-oxatetracyclo<10.2.1.0^3,12.0^7,11>pentadecan-9-one

C₂₅H₃₀O₆S

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