endo-2-hydroxy-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexyl methanesulfonate

Base Information

• Chemical Name: endo-2-hydroxy-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexyl methanesulfonate
• CAS No.: 75011-46-0
• Molecular Formula: C₂₆H₂₃NO₃S₂
• Molecular Weight: 461.606
• Mol file: 75011-46-0.mol

Synonyms:endo-2-hydroxy-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexyl methanesulfonate

Chemical Property of endo-2-hydroxy-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexyl methanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of endo-2-hydroxy-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexyl methanesulfonate

There total 5 articles about endo-2-hydroxy-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexyl methanesulfonate 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: 90.0%

endo-2-hydroxy-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexane (75011-44-8) + methanesulfonyl chloride (124-63-0) → endo-2-hydroxy-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexyl methanesulfonate (75011-46-0)

Guidance literature:

With triethylamine; at 0 ℃; for 1h;

DOI:10.1021/jo01312a013

Reference yield:

3-oxocyclopent-1-ene-1-carbonitrile (34250-16-3) → endo-2-hydroxy-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexyl methanesulfonate (75011-46-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / diethyl ether / 1080 h / Ambient temperature

2: 1) LDA, 2) HMPA / 1) -78 deg C, 30 min, THF, hexane, 2) room temperature, 1 h

3: 83 percent / NaBH₄ / methanol / 2 h / Ambient temperature

4: 90 percent / triethylamine / 1 h / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; triethylamine; lithium diisopropyl amide; In methanol; diethyl ether;

DOI:10.1021/jo01312a013

Reference yield:

5-cyano-6,6-diphenylbicyclo<3.1.0>hexan-2-one (75011-39-1) → endo-2-hydroxy-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexyl methanesulfonate (75011-46-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) LDA, 2) HMPA / 1) -78 deg C, 30 min, THF, hexane, 2) room temperature, 1 h

2: 83 percent / NaBH₄ / methanol / 2 h / Ambient temperature

3: 90 percent / triethylamine / 1 h / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; triethylamine; lithium diisopropyl amide; In methanol;

DOI:10.1021/jo01312a013

upstream raw materials:

endo-2-hydroxy-exo-3-(phenylsulfenyl)-5-cyano-6,6-diphenylbicyclo<3.1.0>hexane

methanesulfonyl chloride

3-oxocyclopent-1-ene-1-carbonitrile

5-cyano-6,6-diphenylbicyclo<3.1.0>hexan-2-one