(1S,2R,4R)-1-[(Z)-2-(4-Chloro-benzenesulfonyl)-vinylsulfanylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol

Base Information

• Chemical Name: (1S,2R,4R)-1-[(Z)-2-(4-Chloro-benzenesulfonyl)-vinylsulfanylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol
• CAS No.: 99908-18-6
• Molecular Formula: C₁₈H₂₃ClO₃S₂
• Molecular Weight: 386.964

Synonyms:(1S,2R,4R)-1-[(Z)-2-(4-Chloro-benzenesulfonyl)-vinylsulfanylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol

Chemical Property of (1S,2R,4R)-1-[(Z)-2-(4-Chloro-benzenesulfonyl)-vinylsulfanylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol

Chemical Property:

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Technology Process of (1S,2R,4R)-1-[(Z)-2-(4-Chloro-benzenesulfonyl)-vinylsulfanylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol

There total 2 articles about (1S,2R,4R)-1-[(Z)-2-(4-Chloro-benzenesulfonyl)-vinylsulfanylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol 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: 62.0%

((p-chlorophenyl)sulfonyl)acetylene (32501-91-0) + (1S,2R,4R)-(-)-10-mercaptoisoboneol (71242-58-5) → (1S,2R,4R)-1-[(Z)-2-(4-Chloro-benzenesulfonyl)-vinylsulfanylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol (99908-18-6)

Guidance literature:

With morpholine; In acetonitrile; for 18h; Ambient temperature;

DOI:10.1021/jo00359a014

Reference yield:

Camphorsulfonyl chloride (21286-54-4) → (1S,2R,4R)-1-[(Z)-2-(4-Chloro-benzenesulfonyl)-vinylsulfanylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol (99908-18-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / LiAlH₄

2: morpholine / acetonitrile

With lithium aluminium tetrahydride; morpholine; In acetonitrile;

DOI:10.1039/C39850000878

Reference yield:

(1S,2R,4R)-1-[(Z)-2-(4-Chloro-benzenesulfonyl)-vinylsulfanylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol (99908-18-6) → (1S,2R,4R)-1-[(S)-(Z)-2-(4-Chloro-benzenesulfonyl)-ethenesulfinylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol (99946-18-6) + (1S,2R,4R)-1-[(R)-(Z)-2-(4-Chloro-benzenesulfonyl)-ethenesulfinylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol (99894-22-1)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In methanol; at -20 ℃;

DOI:10.1021/jo00359a014

upstream raw materials:

((p-chlorophenyl)sulfonyl)acetylene

(1S,2R,4R)-(-)-10-mercaptoisoboneol

Camphorsulfonyl chloride

Downstream raw materials:

(1S,2R,4R)-1-[(Z)-2-(4-Chloro-benzenesulfonyl)-ethenesulfinylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol

(1S,2R,4R)-1-[(E)-2-(4-Chloro-benzenesulfonyl)-vinylsulfanylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol

(1S,4S,6R,8R)-4-(4-Chloro-benzenesulfonylmethyl)-11,11-dimethyl-5-oxa-3-thia-tricyclo[6.2.1.0^1,6]undecane

(1S,4R,6R,8R)-4-(4-Chloro-benzenesulfonylmethyl)-11,11-dimethyl-5-oxa-3-thia-tricyclo[6.2.1.0^1,6]undecane

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