(1S,2S,6R,7R)-1-Methyl-9-phenylsulfanyl-4,10-dioxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

Base Information

• Chemical Name: (1S,2S,6R,7R)-1-Methyl-9-phenylsulfanyl-4,10-dioxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione
• CAS No.: 117707-07-0
• Molecular Formula: C₁₅H₁₂O₄S
• Molecular Weight: 288.324

Synonyms:(1S,2S,6R,7R)-1-Methyl-9-phenylsulfanyl-4,10-dioxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

Chemical Property of (1S,2S,6R,7R)-1-Methyl-9-phenylsulfanyl-4,10-dioxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of (1S,2S,6R,7R)-1-Methyl-9-phenylsulfanyl-4,10-dioxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

There total 6 articles about (1S,2S,6R,7R)-1-Methyl-9-phenylsulfanyl-4,10-dioxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 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: 95.0%

maleic anhydride (108-31-6) + 2-Methyl-3-phenylsulfanyl-furan (105621-16-7) → (1S,2S,6R,7R)-1-Methyl-9-phenylsulfanyl-4,10-dioxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (117707-07-0)

Guidance literature:

DOI:10.1016/S0040-4039(00)83961-1

Reference yield:

2-<2-(phenylthio)ethyl>-1,3-dioxolane (56161-48-9) → (1S,2S,6R,7R)-1-Methyl-9-phenylsulfanyl-4,10-dioxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (117707-07-0)

Guidance literature:

Multi-step reaction with 5 steps

1: N-chlorosuccinimide / CCl₄ / 3 h / 25 °C

2: potassium tert-butoxide / tetrahydrofuran / 4.5 h / 25 °C

3: 1.) sec-butyllithium / 1.) DME, cyclohexane, from -78 deg C to -40 deg C, 15 min, 2.) from -78 deg C to 0 deg C

4: d-camphorsulfonic acid / methanol / 2 h / 25 °C

5: CHCl₃ / 12 h / 25 °C

With N-chloro-succinimide; (1S)-10-camphorsulfonic acid; potassium tert-butylate; sec.-butyllithium; In tetrahydrofuran; methanol; tetrachloromethane; chloroform;

DOI:10.1021/jo00262a024

Reference yield:

(E)-2-<2-(phenylthio)ethenyl>-1,3-dioxolane (105621-12-3) → (1S,2S,6R,7R)-1-Methyl-9-phenylsulfanyl-4,10-dioxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (117707-07-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) sec-butyllithium / 1.) DME, cyclohexane, from -78 deg C to -40 deg C, 15 min, 2.) from -78 deg C to 0 deg C

2: d-camphorsulfonic acid / methanol / 2 h / 25 °C

3: CHCl₃ / 12 h / 25 °C

With (1S)-10-camphorsulfonic acid; sec.-butyllithium; In methanol; chloroform;

DOI:10.1021/jo00262a024

upstream raw materials:

maleic anhydride

2-Methyl-3-phenylsulfanyl-furan

2-<2-(phenylthio)ethyl>-1,3-dioxolane

(+/-)-2-<2-chloro-2-(phenylthio)ethyl>-1,3-dioxolane

Downstream raw materials:

4-methyl-5-(phenylthio)-7-oxabicyclo<2.2.1>hept-5-ene-2-exo,3-exo-dimethanol

(1S,2S,6R,7S,9S)-1-Methyl-9-phenylsulfanyl-4,10-dioxa-tricyclo[5.2.1.0^2,6]decane-3,5-dione

2-exo,3-exo-diethenyl-4-methyl-5-(phenylthio)-7-oxabicyclo<2.2.1>heptane

(1R,2S,3R,4R,5R)-4-Methyl-5-phenylsulfanyl-3-vinyl-7-oxa-bicyclo[2.2.1]heptane-2-carbaldehyde

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