(S)-2-Chloro-hexanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

Base Information

• Chemical Name: (S)-2-Chloro-hexanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
• CAS No.: 104897-96-3
• Molecular Formula: C₂₈H₄₈ClNO₄S
• Molecular Weight: 530.212
• Mol file: 104897-96-3.mol

Synonyms:(S)-2-Chloro-hexanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

Chemical Property of (S)-2-Chloro-hexanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Chloro-hexanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

There total 37 articles about (S)-2-Chloro-hexanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 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: 67.0%

N,N-Dicyclohexyl-C-[(1S,2R,4R)-7,7-dimethyl-2-((E)-1-trimethylsilanyloxy-hex-1-enyloxy)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide (104897-89-4) → (R)-2-Chloro-hexanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester (104897-96-3) + (S)-2-Chloro-hexanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester (104897-96-3)

Guidance literature:

With N-chloro-succinimide; In tetrahydrofuran; Yields of byproduct given. Title compound not separated from byproducts; 1.) -78 deg C, 3 h 2.) 0 deg C, 30 min. d.e. 96 percent;

Reference yield: 67.0%

N,N-Dicyclohexyl-C-[(1S,2R,4R)-7,7-dimethyl-2-((E)-1-trimethylsilanyloxy-hex-1-enyloxy)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide (104897-89-4) → (R)-2-Chloro-hexanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester (104897-96-3) + (S)-2-Chloro-hexanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester (104897-96-3)

Guidance literature:

With N-chloro-succinimide; In tetrahydrofuran; Yields of byproduct given. Title compound not separated from byproducts; 1.) -78 deg C, 3 h 2.) 0 deg C, 30 min. d.e. 96 percent;

Reference yield:

(-)-10-dicyclohexylsulfamoyl-D-isoborneol (96303-88-7) → (S)-2-Chloro-hexanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester (104897-96-3)

Guidance literature:

Multi-step reaction with 7 steps

1: AgCN

2: 1.) n-BuLi, diisopropylamine / 1.) THF, hexane, - 78 deg C 2.) -78 deg C, 1 h.

3: 66 percent / N-Bromo-succinimide / 1,2-dimethoxy-ethane / 0.5 h / -78 °C / d.e. 96percent

4: 90 percent / Ca(BH₄)2 / tetrahydrofuran

5: AgCN

6: 1.) n-BuLi, diisopropylamine / 1.) THF, hexane, - 78 deg C 2.) -78 deg C, 1 h.

7: 67 percent / N-Chloro-succinimide / tetrahydrofuran / 1.) -78 deg C, 3 h 2.) 0 deg C, 30 min. d.e. 96 percent

With N-chloro-succinimide; N-Bromosuccinimide; n-butyllithium; calcium borohydride; silver cyanide; diisopropylamine; In tetrahydrofuran; 1,2-dimethoxyethane;

upstream raw materials:

(-)-10-dicyclohexylsulfamoyl-D-isoborneol

<(2S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> 4-methylvalerate

N,N-Dicyclohexyl-C-[(1S,2R,4R)-7,7-dimethyl-2-((E)-1-trimethylsilanyloxy-hex-1-enyloxy)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide

N,N-Dicyclohexyl-C-[(1S,2R,4R)-7,7-dimethyl-2-((E)-4-methyl-1-trimethylsilanyloxy-pent-1-enyloxy)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide

Downstream raw materials:

(-)-10-dicyclohexylsulfamoyl-D-isoborneol

(S)-2-Chloro-hexan-1-ol

(R)-1,2-epoxyhexane

<(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl>propionate