96303-88-7

Usage

Uses

Used in Chromatography Industry:
(+)-N,N-Dicyclohexyl-(1R)-isoborneol-10-sulfonamide is used as a chiral stationary phase for the separation of enantiomers in chromatographic processes. Its high melting point and low water solubility make it particularly suitable for high-temperature separations, enhancing the efficiency and selectivity of enantiomeric resolution.
Used in Asymmetric Synthesis:
In the field of asymmetric synthesis, (+)-N,N-Dicyclohexyl-(1R)-isoborneol-10-sulfonamide serves as a resolving agent, facilitating the production of enantiomerically pure compounds. This is crucial for the synthesis of pharmaceuticals and agrochemicals where the desired biological activity is often associated with a specific enantiomer.
Used in Metal Ion Separation and Detection:
(+)-N,N-Dicyclohexyl-(1R)-isoborneol-10-sulfonamide is utilized for its metal ion complexing properties in applications involving metal ion separations and detection. Its capacity to form stable complexes with metal ions is valuable in analytical chemistry for the precise identification and quantification of metal content in various samples.
Used in Antimicrobial and Antimalarial Research:
(+)-N,N-DICYCLOHEXYL-(1R)-ISOBORNEOL-10-SULFONAMIDE is explored for its potential as an antimicrobial and antimalarial agent, indicating its use in the development of new therapeutics to combat resistant strains of bacteria and parasites, respectively. This research avenue could lead to innovative treatments in the fields of infectious diseases and tropical medicine.

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-/m0/s1

Upstream product

• 41348-33-8 (1S,5R,7R)-10,10-dimethyl-4-oxa-3-thiatricyclo[5.2.1.0^1,5]decane 3,3-dioxide 
• 3087-36-3 titanium (IV) ethoxide 
• 110449-46-2 <(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> (2R)-2-aminopropionate 
• 110449-47-3 <(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> (2R)-2-aminobutyrate 
• 110449-48-4 <(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> (2R)-2-aminovalerate 
• 110449-49-5 <(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> (2R)-2-aminoisovalerate 
• 110449-50-8 <(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> (2R)-2-amino-4-methylvalerate 
• 110449-51-9 <(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> (2R)-2-aminohexanoate 
• 110449-52-0 <(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> (2S)-2-aminooctanate 
• 110449-53-1 <(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> (2S)-2-amino-3-cyclohexylpropionate 
• 96303-87-6 N,N-dicyclohexylcamphor-10-sulfonamide 
• 104897-87-2 (S)-3-Methyl-hexanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 104897-94-1 (S)-2-Chloro-propionic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 104897-98-5 (S)-2-Bromo-4-methyl-pentanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 

Downstream Products

• 121703-15-9 10-dicyclohexylsulfamoyl-D-isobornyl chloroformate 
• 121767-99-5 Pyridin-4-yl-acetic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 96864-12-9 (E)-Hex-2-enoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 104898-08-0 (1S,2R,4R)-1-(N,N-dicyclohexylaminosulfonylmethyl)-7,7-dimethylbicyclo<2.2.1>heptan-2-yl crotonate 
• 104926-26-3 <(2S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> 4-methylvalerate 
• 188183-27-9 (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyanopropanoate 
• 188183-29-1 (2RS)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 3-methyl-2-cyanobutanoate 
• 96864-31-2 <(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl>propionate 
• 96864-08-3 <(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> hexanoate 
• 106748-94-1 <(1S,2R)-10-(N,N,-dicyclohexylaminosulfonyl)born-2-yl> valerate 
• 104975-04-4 Decanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 109106-00-5 Acetic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 106748-93-0 <(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl>butanoate 
• 130156-92-2 2-O-(chloroacetyl)-10-(dicyclohexylsulfamoyl)-D-isoborneol 

Relevant academic research and scientific papers

Application in asymmetric Morita-Baylis-Hillman reactions

N-Substituted 2-exo-hydroxybornyl-10-sulfonamides, prepared as potential chiral auxiliaries for use in asymmetric Morita-Baylis-Hillman (MBH) reactions, have been treated with acryloyl chloride to afford the corresponding 2-exo-Acrylate esters as MBH subs

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

Diastereoselectivity in the Preparation of β-Silyl Esters from αβ-Unsaturated Esters and Amides Attachhed to Chiral Auxiliaries

The conjugate addition of the phenyldimethylsilyl-cuprate reagent to cinnamate and crotonate esters and amides 1 of various known chiral auxiliaries, a-e, is diastereoselective.The sense of diastereoselectivity of silyl-cuprate addition to the esters 1b-d, 8 and 9 is different from established precedent based on carbon-cuprates, but is normal for silyl-cuprate addition to the amide 1a, the imines 1e and 21, and the oxazolidine 6.The chiral auxiliary e gives the best results of those tested, and the silicon-containing group can be removed from the chiral auxiliary using alkoxide ion in aprotic media, making available β-silyl esters 27-29 of high enantiomeric excess, with recovery of the chiral auxiliary 30.

Chiral acrylates as substrates in Baylis-Hillman reaction

DABCO induces diastereoselective (7-70%) coupling of chiral acrylates (1-3) with aldehydes to produce the corresponding 2-(1-hydroxyalkyl)acrylates.

NEW SYNTHESIS OF THE CALIFORNIA RED SCALE SEX PHEROMONE

The target molecules 1 and 2 were synthesized from a common intermediate 6 prepared from (R)-Limonene.The first enantioselective synthesis of 2 is described.

ENANTIOSELECTIVE SYNTHESES OF α-AMINO ACIDS FROM 10-SULFONAMIDO-ISOBORNYL ESTERS AND DI-t-BUTYL AZODICARBOXYLATE

Successive treatment of chiral esters 7 with LDA/Me3SiCl and di-t-butyl azodicarboxylate/TiCl4 and Ti(OiPr)4 gave N,N-di-t-butoxycarbonylhydrazinoesters 11 which on deacylation, hydrogenolysis, transesterification and acidic hydrolysis furnished (2S)-α-amino acid hydrochlorides 13 in good overall yields, high enantiomeric purity and with efficient recovery of the alcohol auxiliary 4.Experimental evidence for the configuration and conformation of the intermediate O-silyl ketene acetals 1 is provided.

Camphorsulfonamide-Shielded, Asymmetric 1,4-Additions and Enolate Alkylations; Synthesis of a Southern Corn Rootworm Pheromone

Using readily accessible 10-sulfonamido-isoborneols as regenerable, chiral auxiliaries, highly face-selective C-C-bond formations at Cα and Cβ of carboxylates could be conveniently achieved.Thus, conjugated additions of RCu to enoates (1->2) furnished, after saponification, β-substituted carboxylic acids 3 in 94-98 percent e.e.Similarly, propionates 12 yielded after deprotonation, enolate alkylation, and reductive ester cleveage the (R)-alcohols 15 in 78-98 percent e.e.The acid (+)-3e was converted to the pheromone (-)-11.

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..

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