94594-90-8

Basic information

• Product Name: (2R)-Bornane-10,2-sultam
• Synonyms: (-)-EXO-10,2-BORNANESULTAM;(-)-D-2,10-CAMPHORSULTAM;(-)-D-2,10-CAMPHOSULTAM;D(-)-10,2-CAMPHORSULTAME;(2R)-BORNANE-10,2-SULTAM;(1S)-(-)-2,10-CAMPHORSULTAM;(1S)-2,10-CAMPHORSULTAM;(1S,2R)-(-)-2,10-CAMPHORSULTAM
• CAS NO: 94594-90-8
• Molecular Formula: C₁₀H₁₇NO₂S
• Molecular Weight: 215.31
• Product Categories: chiral;Asymmetric Synthesis;Bicyclic Monoterpenes;Biochemistry;Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;Terpenes;Peptide;Chiral Reagents;Sulfur & Selenium Compounds
• Mol File: 94594-90-8.mol
• Article Data: 44

Chemical Properties

• Melting Point: 183-185 °C
• Boiling Point: 324.8 °C at 760 mmHg
• Flash Point: 150.3 °C
• Appearance: Clear colorless/Liquid
• Density: 1.1469 (rough estimate)
• Vapor Pressure: 0.000239mmHg at 25°C
• Refractive Index: -31 ° (C=1, CHCl3)
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Ethanol, Methanol
• PKA: 11.05±0.40(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 83811
• CAS DataBase Reference: (2R)-Bornane-10,2-sultam(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-Bornane-10,2-sultam(94594-90-8)
• EPA Substance Registry System: (2R)-Bornane-10,2-sultam(94594-90-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• Hazardous Substances Data: 94594-90-8(Hazardous Substances Data)

Usage

Description

(2R)-Bornane-10,2-sultam is a white to light yellow crystalline powder that serves as a crucial reagent in the synthesis of various organic compounds, particularly in the preparation of Camphorsultam conjugates. It plays a significant role in asymmetric synthesis, chiral probe applications, and other asymmetric transformations.

Uses

Used in Organic Synthesis:
(2R)-Bornane-10,2-sultam is used as a reagent for the preparation of Camphorsultam conjugates, which are essential in various organic synthesis processes.
Used in Asymmetric Synthesis:
In the field of asymmetric synthesis, (2R)-Bornane-10,2-sultam is used as a proton source in the synthesis of chiral α,γ-substituted γ-butyrolactones. It is also employed in the asymmetric synthesis of (S)and (R)-N-Fmoc-S-trityl-α-methylcysteine, a crucial component in peptide synthesis.
Used as a Chiral Probe:
(2R)-Bornane-10,2-sultam serves as a chiral probe for optical resolution by High-Performance Liquid Chromatography (HPLC) and X-ray crystallographic determination of the absolute stereochemistry of carboxylic acids. This application is vital in the analysis and separation of enantiomers, which are essential in various industries, including pharmaceuticals and agrochemicals.
Used in Dienophile Preparation:
(2R)-Bornane-10,2-sultam is also used to prepare N-acryloyl derivatives, which are employed as dienophiles in asymmetric Diels-Alder reactions. These reactions are crucial in the synthesis of complex organic molecules with specific stereochemistry.
Overall, (2R)-Bornane-10,2-sultam is a versatile reagent with applications in various fields of organic chemistry, including asymmetric synthesis, chiral probe applications, and the preparation of intermediates for complex organic molecules. Its unique properties make it an essential component in the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.

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+/m0/s1

Upstream product

• 60886-80-8 (1S)-(-)-camphorsulfonylimine 
• 186581-53-3 diazomethane 
• 125664-99-5 N-<(2R,3S)-3-hydroxy-2-methylbutanoyl>bornane-10,2-sultam 
• 125665-01-2 N-<(2R,3S)-3-hydroxy-2,4-dimethylpentanoyl>bornane-10,2-sultam 
• 125760-65-8 N-<(2S,3R)-3-hydroxy-2,4-dimethylpentanoyl>bornane-10,2-sultam 
• 125665-08-9 N-<(2S,3R)-3-hydroxy-2-methylhexenoyl>bornane-10,2-sultam 
• 125665-06-7 N-<(2S,3R)-2-ethyl-3-hydroxy-4-methylpentanoyl>bornane-10,2-sultam 
• 125665-02-3 N-<(2S,3R)-2-methyl-3-hydroxy-(E)-4-hexenoyl>bornane-10,2-sultam 
• 125665-09-0 N-<(2S,3R)-2-ethyl-3-hydroxy-(E)-hexenoyl>bornane-10,2-sultam 
• 125664-98-4 (2R,3R)-1-((6R)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)-3-hydroxy-2-methyl-3-phenylpropan-1-one 
• 125760-63-6 N-<(2S,3R)-2-methyl-3-hydroxy-3-phenylpropanoyl>bornane-10,2-sultam 
• 125665-04-5 N-<(2R,3R)-2-(hydroxybenzyl)butanoyl>bornane-10,2-sultam 
• 125665-04-5 N-<(2S,3S)-2-(hydroxybenzyl)butanoyl>bornane-10,2-sultam 
• 64-17-5 ethanol 

Downstream Products

• 94668-55-0 (1S)-N-crotyl-2,10-camphorsultam 
• 94594-91-9 acrylcamphorsultam 
• 121560-18-7 (3aS,6R,7aR)-1-(cyclohex-1-en-1-ylcarbonyl)-8,8-dimethylhexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide 
• 157518-33-7 4-[(E)-3-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-oxo-propenyl]-benzonitrile 
• 157604-00-7 (E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(3-methoxy-phenyl)-propenone 
• 116195-24-5 (2-methyl-3-phenyl-butanoyl)bornane-10,2-sultam 
• 138566-17-3 2-(benzhydrylideneamino)-1-(10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1.5]dec-4-yl)ethanone 
• 125664-95-1 N-propionyl-(2R)-bornane-(10,2)-sultam 
• 141993-16-0 1-[(1S,5R)-10,10-dimethyl-3,3-dioxido-3-thia-4-azatricyclo[5.2.1.0^1.5]dec-4-yl]-ethanone 
• 157603-99-1 (E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(2-methoxy-phenyl)-propenone 
• 121560-17-6 N-<(E)-2-methyl-3-phenyl-2-propenoyl>bornane-10,2-sultam 
• 109053-73-8 (3aS,6R,7aR)-8,8-dimethyl-1-[(2E)-3-phenylprop-2-enoyl]hexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide 
• 157604-01-8 (E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(3,4,5-trimethoxy-phenyl)-propenone 
• 157604-02-9 (E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(5-fluoro-2-methoxy-phenyl)-propenone 

Relevant articles and documents

Palladium-Catalyzed Stereoselective Cyclization of in Situ Formed Allenyl Hemiacetals: Synthesis of Rosuvastatin and Pitavastatin

A diastereoselective palladium-catalyzed cyclization of allenyl hemiacetals is described. It permits the selective synthesis of 1,3-dioxane derivatives, precursors for syn-configured 1,3-diols which make an appearance in all of the statin representatives. The reaction allows the total synthesis of Rosuvastatin and Pitavastatin in a straightforward fashion.

Tosvinyl and besvinyl as protecting groups of imides, azinones, nucleosides, sultams, and lactams. Catalytic conjugate additions to tosylacetylene

The use of the 2-(4-methylphenylsulfonyl)-ethenyl (tosvinyl, Tsv) group for the protection of the NH group of a series of imides, azinones (including AZT), inosines, and cyclic sulfonamides has been examined. The Tsvprotected derivatives are obtained in excellent yields by conjugate addition to tosylacetylene (ethynyl p-tolyl sulfone). The stereochemistry of the double bond can be controlled at will: with only 1 mol % of Et3N or with catalytic amounts of NaH, the Z stereoisomers are generated almost exclusively, while the E isomers are obtained using a stoichiometric amount of DMAP. Analogous phenylsulfonylvinyl-protected groups (with the besvinyl or Bsv group instead of Tsv) are obtained stereospecifically by reaction with (Z)- or (E)-bis(phenylsulfonyl)ethene. For lactams and oxazolidinones, this last method is much better. The Tsv and Bsv groups are stable in the presence of non-nucleophilic bases and to acids. They can be removed highly effectively via a conjugate addition-elimination mechanism using pyrrolidine or sodium dodecanethiolate as nucleophiles.

A facile, inexpensive and scalable route to thiol-protected α-methyl cysteine

A facile, scalable synthesis of α-methyl cysteine with three alternate thiol protecting groups (trityl, allyl and tert-butyl) is described. The thiol-protected amino acids are obtained in six steps from l-cysteine ethyl ester and are ideally suited for a range of natural product and solid-phase peptide synthesis applications. Georg Thieme Verlag Stuttgart - New York.