99295-72-4

Usage

Uses

Used in Pharmaceutical Industry:
(-)-N,N-Dicyclohexyl-(1S)-isoborneol-10-sulfonamide is used as a chiral auxiliary in the synthesis of pharmaceutical compounds for controlling the stereochemistry of reactions and improving the selectivity and yield of desired enantiomers.
Used in Organic Synthesis:
(-)-N,N-Dicyclohexyl-(1S)-isoborneol-10-sulfonamide is used as a chiral auxiliary in various organic reactions for controlling the stereochemistry and enhancing the selectivity of the reactions, leading to the production of enantiomerically pure compounds.
Used in Asymmetric Catalysis:
(-)-N,N-Dicyclohexyl-(1S)-isoborneol-10-sulfonamide is used as a chiral ligand in asymmetric catalysis to control the enantioselectivity of catalytic reactions, enabling the synthesis of enantiomerically pure products with high yields and selectivity.

InChI:InChI=1/C22H39NO3S/c1-21(2)17-13-14-22(21,20(24)15-17)16-27(25,26)23(18-9-5-3-6-10-18)19-11-7-4-8-12-19/h17-20,24H,3-16H2,1-2H3/t17-,20-,22-/m1/s1

Upstream product

• 104926-28-5 (R)-2-Bromo-decanoic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-27-2 (S)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-16-9 (S)-2-(4-Methoxy-benzylamino)-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-14-7 (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-19-2 (S)-2-[(2-Chloro-acetyl)-(4-methoxy-benzyl)-amino]-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 96864-09-4 Decanoic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 104926-27-4 N,N-Dicyclohexyl-C-[(1R,2S,4S)-7,7-dimethyl-2-((E)-1-trimethylsilanyloxy-dec-1-enyloxy)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 96864-05-0 (E)-But-2-enoic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 96864-09-4 Decanoic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 130195-80-1 Chloro-acetic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 157766-05-7 Pent-4-enoic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 172477-07-5 (1R,2S,4S)-(+)-1-dicyclohexylsulfamoylmethyl-7,7-dimethylbicyclo<2.2.1>hept-2-yl hexadecanoate 
• 439589-15-8 (S)-2-Benzyloxycarbonylamino-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-14-7 (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-26-1 (S)-2-[Benzyloxycarbonyl-(4-methoxy-benzyl)-amino]-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-24-9 (S)-2-[Benzyloxycarbonyl-(4-methoxy-benzyl)-amino]-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 888034-62-6 (+)-(1R,2S,4S)-N,N-dicyclohexyl-7,7-dimethyl-2-propynoyloxybicyclo[2.2.1]heptane-1-methanesulfonamide 
• 888034-68-2 (+)-(1R,2S,4S)-N,N-dicyclohexyl-7,7-dimethyl-2-(3-(2,4,6-trimethylphenyl)isoxazole-4-carboxy)bicyclo[2.2.1]heptane-1-methanesulfonamide 
• 888034-75-1 (+)-(1R,2S,4S)-N,N-dicyclohexyl-7,7-dimethyl-2-(5-methyl-3-(2,4,6-trimethylphenyl)isoxazole-4-carboxy)bicyclo[2.2.1]heptane-1-methanesulfonamide 
• 121666-46-4 (R)-{(1R,2S,4S)-1-[(Dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yloxycarbonylamino}-(4-methoxy-phenyl)-acetic acid methyl ester 
• 141936-52-9 2,3-Dichloro-propionic acid (1S,2R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 

Relevant academic research and scientific papers

General approach for the stereocontrolled construction of the beta-lactam ring in amino acid-derived 4-alkyl-4-carboxy-2-azetidinones.

The first general approach toward the asymmetric synthesis of 4-alkyl-4-carboxy-2-azetidinones derived from amino acids is described. The stereoselective construction of the beta-lactam ring was achieved through base-mediated intramolecular cyclization of the corresponding N(alpha)-chloroacetyl derivatives bearing (+)- or (-)-10-(N,N-dicyclohexylsulfamoyl)isoborneol as chiral auxiliary (ee up to 82%).

Synthesis of new fluorine-containing taxoids by means of β-lactam synthon method

A series of new fluorine-containing analogs of paclitaxel and docetaxel are synthesized using the coupling of (3R,4S)-1-acyl-β-lactams with high enantiomeric purity with properly protected baccatin III, 10-deacetylbaccatin III, and 14β-hydroxy-10-deacetyl

Asymmetric α-Acetoxylation of Carboxylic Esters

Using the readily accessible chiral auxiliaries 1-3 the sulfonamide-shielded O-silylated esters 5 underwent ?-face-selective α-acetoxylation on successive treatment with Pb(OAc)4 and NEt3*HF to give after recrystallization α-acetoxy ester 6 in 55-66percen

ASYMMETRIC HALOGENATION OF CAMPHOR-10-SULFONIC ACID DERIVED ESTERS: AN EFFICIENT NEW ROUTE TO ENANTIOMERICALLY PURE HALOHYDRINS AND EPOXIDES.

Successive treatment of chiral esters 1 with LDA/Me3SiCl and NBS or NCS gave crystalline α-haloesters 3 which furnished halohydrins 4 and terminal epoxides 5 in high e.e..