108448-77-7

Basic information

• Product Name: (2S)-Bornane-10,2-sultam
• Synonyms: (7aS)-8,8-Dimethylhexahydro-1H-3a,6-methanobenzo[c]isothiazole 2,2-dioxide;(2S)-Borne-10,2-sultam;L-2,10-Camphorsultam,99%e.e.;(2S)-BORNANE-10,2-SULTAM;(1R)-(+)-2,10-CAMPHORSULTAM;(1R)-2,10-CAMPHORSULTAM;(1R,2S)-(+)-2,10-CAMPHORSULTAM;(1R,5S)-10,10-DIMETHYL-3-THIA-4-AZATRICYCLO[5.2.1.01,5]DECANE 3,3-DIOXIDE
• CAS NO: 108448-77-7
• Molecular Formula: C₁₀H₁₇NO₂S
• Molecular Weight: 215.31
• Product Categories: chiral;Asymmetric Synthesis;Bicyclic Monoterpenes;Biochemistry;Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;Terpenes;Peptide
• Mol File: 108448-77-7.mol

Chemical Properties

• Melting Point: 185-187 °C(lit.)
• Boiling Point: 324.8 °C at 760 mmHg
• Flash Point: 150.3 °C
• Appearance: white to light yellow crystal powder
• Density: 1.1469 (rough estimate)
• Vapor Pressure: 0.000239mmHg at 25°C
• Refractive Index: 31 ° (C=1, CHCl3)
• Storage Temp.: 2-8°C
• Solubility: almost transparency in Chloroform
• PKA: 11.05±0.40(Predicted)
• BRN: 4675755
• CAS DataBase Reference: (2S)-Bornane-10,2-sultam(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-Bornane-10,2-sultam(108448-77-7)
• EPA Substance Registry System: (2S)-Bornane-10,2-sultam(108448-77-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 108448-77-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2S)-Bornane-10,2-sultam is used as a reactant for the synthesis of pyrrolidine acid analogs, which are potent dual PPARα/γ agonists. These agonists play a crucial role in the development of medications targeting metabolic disorders and other related health conditions.
Used in Chemical Synthesis:
(2S)-Bornane-10,2-sultam is utilized as an intermediate in the synthesis of various organic compounds, contributing to the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research and Development:
Due to its unique chemical properties, (2S)-Bornane-10,2-sultam is employed in research and development for the exploration of new chemical reactions, mechanisms, and the creation of novel molecular structures with potential applications in various industries.

Purification Methods

The (-)-enantiomer is recrystallised from 95% EtOH and dried in a vacuum desiccator. It dissolves in dilute aqueous NaOH and can be precipitated without hydrolysis by acidifying. It forms the N-Na salt in EtOH (by addition of Na to the EtOH solution), and the salt can be methylated with MeI to give the (-)-N-Me lactam with m 80o after recrystallisation from hot H2O and has []D -59.6o (c 5, CHCl3) [Shriner et al. J Am Chem Soc 60 2794 1938]. [Oppolzer et al. Helv Chim Acta 69 1142 1986, Weismiller et al. Org Synth 69 154 1955, Beilstein 27 III/IV 1007.]

InChI:InChI=1/C10H17NO2S/c1-9(2)7-3-4-10(9)6-14(12,13)11-8(10)5-7/h7-8,11H,3-6H2,1-2H3/t7-,8-,10+/m1/s1

Upstream product

• 104319-35-9 DL camphor-10-thiazine dioxide 
• 119944-89-7 (2S)-N-(acryloyl)bornane-10,2-sultam 
• 35963-20-3 (R)-10-camphorsulfonic acid 
• 107869-45-4 (+)-(camphorylsulfonyl)imine 
• 100-53-8 phenylmethanethiol 
• 193416-18-1 (E)-(R)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2,4-dimethyl-hept-4-en-1-one 
• 193416-13-6 (S)-2-[(4R,5S,6S)-2,2-Di-tert-butyl-6-((S)-1-[1,3]dithiolan-2-yl-ethyl)-5-methyl-[1,3,2]dioxasilinan-4-yl]-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-propan-1-one 
• 542-92-7 cyclopenta-1,3-diene 
• 188845-76-3 (7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^3,7]decane-4-hydroxamic acid 
• 78607-52-0 2-aza-3-oxabicyclo(2.2.1)hept-5-ene hydrochloride 
• 872-36-6 vinylene carbonate 
• 153440-80-3 ((R)-1-Benzyl-aziridin-2-yl)-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone 
• 941-69-5 N-phenyl-maleimide 
• 100-52-7 benzaldehyde 

Downstream Products

• 94594-81-7 (E)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)but-2-en-1-one 
• 128947-19-3 (2S)-N-propionylcamphorsultam 
• 119944-89-7 (2S)-N-(acryloyl)bornane-10,2-sultam 
• 143097-08-9 (1S,7R)-4-<3-<(1S,7R)-10,10-dimethyl-5,5-dioxo-5-thia-4-azatricyclo<5.2.1.0^3,7>dec-4-yl>propanoyl>-10,10-dimethyl-5-thia-4-azatricyclo<5.2.1.0^3,7>decane 5,5-dioxide 
• 128441-99-6 (3aR-(3aα,6α,7aβ))-hexahydro-8,8-dimethyl-1-(2-methyl-1-oxo-2-propenyl)-3H-3a,6-methano-2,1-benzisothiazole 2,2-dioxide 
• 129505-04-0 (2S)-N-<(4-methoxyphenyl)acetyl>bornane-10,2-sultam 
• 155487-36-8 2-Benzyloxy-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-ethanone 
• 155396-70-6 N-<<(p-Methoxybenzyl)oxy>acetyl>-2,10-camphorsultam 
• 192203-86-4 (1R,5S,7S)-1-(10,10-dimethyl-3,3-dioxo-3-thia-4-azatricyclo[5.2.1.0^1,5]decan-4-yl)-3-phenyl-3-propyn-1-one 
• 188650-93-3 1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-(4-isobutyl-phenyl)-ethanone 
• 224578-11-4 Acetic acid 4-[(E)-3-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-oxo-propenyl]-2-methoxy-phenyl ester 
• 233757-46-5 (2S)-N-[10'-(tert-butyldiphenylsilyloxy)dec-6'-ynoyl]bornane-10,2-sultam 
• 188845-76-3 (7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^3,7]decane-4-hydroxamic acid 
• 278793-27-4 N-[(E)-2-[4-(t-butyldimethylsiloxymethyl)benzyloxyimino]ethanonyl]bornane-10,2-sultam 

Relevant articles and documents

14. Origin of Diastereoselectivity in the Thermal [4+2] Cycloadditions of Dienophiles Derived from Oppolzer's Sultams: Steric vs. Stereoelectronic Influences

Comparative semi-empirical PM3 and ab initio STO 3-21G calculations on bornanesultam-derived dienophiles containing the structural moiety SO2-N-C(O)-X(α) = Y(β) suggest that, among the conformers of low energy, the thermodynamically less stable SO2/C(O)-syn,C(O)/X=Y-s-cis conformation is also reactive in terms of LUMO level and atomic coefficients, Furthermore, the X(α), Y(β) LUMO atomic coefficients are nonequivalent with respect to both X(α)-re and X(α)-si faces, and thus have, depending on the conformation, a matching or mismatching stereoelectronic influence with the co-operative steric effect. This dissymmetry is believed to result from the generalized anomeric effect of the N lone pair, itself anomerically stabilized and directed, in the absence of crucial steric interactions, by the pseudo-axial anti-periplanar S=O bond. Five N-acyl-substituted bornanesultams are discussed ((-)-1a: N-acryloyl, X=CH, Y=CH2; (-)-1b: N-crotonoyl, X=CH, Y=CHMe; (-)-1c: N,N'-fumaroyl, X=CH, Y=CH(C(O)-bornanesultam); 2a: N-glyoxyloyl, X=CH, Y=O; 2b: N-acylnitroso, X=N, Y=O). In this context, differences with toluenesultams 3 are pointed out. A previous report on N-(acylnitroso)-bornanesultam 2b is revisited, and the diastereoselectivity observed is shown to result from thermodynamic control.

Asymmetric Electrophilic α-Amination of Silyl Enol Ether Derivatives via the Nitrosocarbonyl Hetero-ene Reaction

The first example of a general asymmetric nitrosocarbonyl hetero-ene reaction is described. The procedure uses a copper-catalyzed aerobic oxidation of a commercially available chiral nitrosocarbonyl precursor (EleNOr) and is operationally simple. The tran

Asymmetric multicomponent [C+NC+CC] synthesis of highly functionalized pyrrolidines catalyzed by silver(I)

Highly functionalized pyrrolidines are obtained in a single chemical step via a mild, efficient, and selective Ag1-catalyzed asymmetric [C+NC+CC] coupling process. Oppolzer's camphorsultam enables the desired reaction cascade and provides a rel

A practical large-scale synthesis of (3R,4R)-4-(Hydroxymethyl)pyrrolidin-3- ol via asymmetric 1,3-dipolar cycloaddition

(3R,4R)-4-(Hydroxymethyl)pyrrolidin-3-ol (1), which is a useful intermediate for the synthesis of various bioactive molecules, has been synthesized in 51% overall yield by 1,3-dipolar cycloaddition reaction from the dipolarophile, (E)-3-benzyloxypropenoyl-(2′S)-bornane-10,2-sultam (5), and the achiral ylide precursor, N-(benzyl)-N-(methoxymethyl)-N- (trimethylsilylmethyl)amine (6), without using chromatography and the subsequent reduction with LAH and catalytic hydrogenation. The diastereomers 7 and 8 were separated by crystallization, and efficient procedures were developed for the subsequent reactions to afford 1.

Stereocontrolled 1,3-dipolar cycloadditions using Oppolzer's camphor sultam as the chiral auxiliary for carbonyl stabilized azomethine ylides

Two complementary approaches to substituted pyrrolidines via stereocontrolled 1,3-dipolar cycloaddition reactions of chiral azomethine ylides are described. In one approach, chiral azomethine ylides were generated by thermolysis of aziridine carboxylate sultams and trapped with a variety of dipolarophiles to give good yields of the corresponding cycloadducts. In the second approach, chiral azomethine ylides were generated from glycyl sultams by 'imine tautomerization' and trapped with dipolarophiles to give good yields of the corresponding cycloadducts.

Progress toward the total synthesis of callipeltin A (I): Asymmetric synthesis of (3S,4R)-3,4-dimethylglutamine

(equation presented) During the total synthesis of the novel cyclic depsipeptide callipeltin A (1), the unit (3S,4R)-3,4-dimethylglutamine, was successfully synthesized by asymmetric Michael addition and subsequent electrophilic azidation. The key feature of this approach is the generation of three adjacent stereogenic centers using the same camphorsultam chiral auxiliary.

Enantioselective total synthesis of (-)-denticulatins A and B using a novel group-selective aldolization of a meso dialdehyde as a key step

The diastereoselective synthesis of (-)-denticulatin A (1a) was achieved for the first time in 9 steps (41% yield) based on a novel group-selective aldolization of a meso dialdehyde as a key step. The inherent chirality present in bornanesultam 4 was thus transmitted to the five stereocenters spanning C4-C8 in key intermediate 8. In addition, denticulatin B (1b) was obtained from the common intermediate 8 en route to denticulatin A in 10 steps and 35% overall yield.

Diastereo- and enantiocontrolled synthesis of (-)-allosedamine via cycloaddition of a chiral nitrone

The piperidine alkaloid (-)-allosedamine (1) has been synthesized, in 21% overall yield, in nine steps starting from the formyl-ester 4. The synthesis features the reaction cascade 7 → 3 → 2, involving asymmetric electrophilic enolate hydroxyamination, hy

A practical synthesis of (R)-(+)-cyclohex-3-enecarboxylic acid via an asymmetric Diels-Alder reaction

The polymerisation which complicates the ethylaluminum dichloride-catalysed asymmetric Diels-Alder reaction between N-propenoylbornane-10,2-sultam[10,10-dimethyl-3-thia-4-azatricyclo[5.2 .1.01,5]decane 3,3-dioxide] and butadiene can be suppress