(1RS,2RS,4SR,5RS,6RS)-2-endo-acetoxy-5-endo-chloro-6-exo-benzenesulfenyl-7-oxabicyclo<2.2.1>heptane-2-exo-carbonitrile

Base Information

• Chemical Name: (1RS,2RS,4SR,5RS,6RS)-2-endo-acetoxy-5-endo-chloro-6-exo-benzenesulfenyl-7-oxabicyclo<2.2.1>heptane-2-exo-carbonitrile
• CAS No.: 101677-60-5
• Molecular Formula: C₁₅H₁₄ClNO₃S
• Molecular Weight: 323.8

Synonyms:(1RS,2RS,4SR,5RS,6RS)-2-endo-acetoxy-5-endo-chloro-6-exo-benzenesulfenyl-7-oxabicyclo<2.2.1>heptane-2-exo-carbonitrile

Chemical Property of (1RS,2RS,4SR,5RS,6RS)-2-endo-acetoxy-5-endo-chloro-6-exo-benzenesulfenyl-7-oxabicyclo<2.2.1>heptane-2-exo-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1RS,2RS,4SR,5RS,6RS)-2-endo-acetoxy-5-endo-chloro-6-exo-benzenesulfenyl-7-oxabicyclo<2.2.1>heptane-2-exo-carbonitrile

There total 2 articles about (1RS,2RS,4SR,5RS,6RS)-2-endo-acetoxy-5-endo-chloro-6-exo-benzenesulfenyl-7-oxabicyclo<2.2.1>heptane-2-exo-carbonitrile 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:

2-endo-acetoxy-7-oxabicyclo<2.2.1>hept-5-ene-2-exo-carbonitrile (79902-01-5,84120-97-8,84120-98-9,84424-28-2,94482-74-3,105497-65-2,120056-66-8,148346-15-0) + benzenesulfenyl chloride (931-59-9) → (1RS,2RS,4SR,5RS,6RS)-2-endo-acetoxy-5-endo-chloro-6-exo-benzenesulfenyl-7-oxabicyclo<2.2.1>heptane-2-exo-carbonitrile (101677-60-5)

Guidance literature:

In dichloromethane; at -78 ℃; Yield given;

DOI:10.1016/S0040-4039(00)98879-8

Reference yield:

2-endo-acetoxy-7-oxabicyclo<2.2.1>hept-5-ene-2-exo-carbonitrile (79902-01-5,84120-97-8,84120-98-9,84424-28-2,94482-74-3,105497-65-2,120056-66-8,148346-15-0) + thiophenol (108-98-5) → (1RS,2RS,4SR,5RS,6RS)-2-endo-acetoxy-5-endo-chloro-6-exo-benzenesulfenyl-7-oxabicyclo<2.2.1>heptane-2-exo-carbonitrile (101677-60-5)

Guidance literature:

With N-chloro-succinimide; Yield given. Multistep reaction; 1.) CH₂Cl₂, 20 deg C, 30 min, 2.) CH₂Cl₂, from -78 deg C to RT;

DOI:10.1021/jo00376a055

Reference yield:

(1RS,2RS,4SR,5RS,6RS)-2-endo-acetoxy-5-endo-chloro-6-exo-benzenesulfenyl-7-oxabicyclo<2.2.1>heptane-2-exo-carbonitrile (101677-60-5) → (1R,2R,4S,5R,6R)-5-Chloro-2-hydroxy-6-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane-2-carbonitrile

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 1h;

DOI:10.1021/jo00376a055

upstream raw materials:

2-endo-acetoxy-7-oxabicyclo<2.2.1>hept-5-ene-2-exo-carbonitrile

thiophenol

benzenesulfenyl chloride

Downstream raw materials:

(1RS,4SR,5RS,6RS)-5-endo-chloro-6-exo-benzenesulfenyl-7-oxa-2-bicyclo<2.2.1>heptanone

(+/-)-7-oxa-2-bicyclo<2.2.1>heptanone

7-oxa-bicyclo[2.2.1]heptan-2-one

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