94668-55-0

Basic information

• Product Name: (N-CROTONYL)-(2R)-BORNANE-10,2-SULTAM
• Synonyms: (R)-(-)-(2-BUTENOYL)-2,10-CAMPHORSULTAM;(N-CROTONYL)-(2R)-BORNANE-10,2-SULTAM;(N-Crotonyl)-(2R)-bornane-10,2-sultam, (2E)-1-[(3aS,6R,7aR)-Tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-2-buten-1-one
• CAS NO: 94668-55-0
• Molecular Formula: C₁₄H₂₁NO₃S
• Molecular Weight: 283.39
• Product Categories: Peptide
• Mol File: 94668-55-0.mol
• Article Data: 10

Chemical Properties

• Melting Point: 180-184 °C(lit.)
• Boiling Point: 397.2°Cat760mmHg
• Flash Point: 194°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 1.62E-06mmHg at 25°C
• Refractive Index: 1.576
• PKA: -14.19±0.40(Predicted)
• CAS DataBase Reference: (N-CROTONYL)-(2R)-BORNANE-10,2-SULTAM(CAS DataBase Reference)
• NIST Chemistry Reference: (N-CROTONYL)-(2R)-BORNANE-10,2-SULTAM(94668-55-0)
• EPA Substance Registry System: (N-CROTONYL)-(2R)-BORNANE-10,2-SULTAM(94668-55-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 94668-55-0(Hazardous Substances Data)

Usage

Uses

(R)-(-)-(2-Butenoyl)-2,10-camphorsultam can be used: In the asymmetric total synthesis of lycopodine via diastereoselective cyclization and intramolecular Mannich cyclization. To prepare (S)-4,4-dichloro-3-methylbutanoic acid, which is utilized as a key intermediate for the total synthesis of dysideaproline E.

InChI:InChI=1/C14H21NO3S/c1-4-5-12(16)15-11-8-10-6-7-14(11,13(10,2)3)9-19(15,17)18/h4-5,10-11H,6-9H2,1-3H3/b5-4+/t10-,11+,14-/m1/s1

Upstream product

• 625-35-4 trans-chrotonyl chloride 
• 94594-90-8 (2R)-bornane-10,2-sultam 
• 623-68-7 trans-crotonic anhydride 
• 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 
• 316823-25-3 (1S,2R)-N-[(3'RS)-3'-Hydroxybutanoyl]bornane-10,2-sultam 
• 3144-16-9 (1S)-10-camphorsulfonic acid 
• 21286-54-4 Camphorsulfonyl chloride 
• 4894-61-5 trans-but-2-enyl chloride 
• 108462-67-5 (2R,3S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2,3-dimethyl-heptan-1-one 
• 60886-80-8 (+/-)-8,8-dimethyl-4,5,6,7-tetrahydro-3ar,6c-methano-benz[c]isothiazole-2,2-dioxide 
• 21286-54-4 (+)-(1S)-Campher-10-sulfonsaeure-chlorid 
• 17854-63-6 (+/-)-2-oxo-bornane-10-sulfonic acid amide 
• 60886-80-8 (1S)-(-)-camphorsulfonylimine 

Downstream Products

• 1422463-22-6 C₁₆H₂₂O₃ 
• 94594-90-8 (2R)-bornane-10,2-sultam 
• 934831-78-4 (+)-(2S)-N-[(3aS,4S,5R,7aS)-2,2-dimethyl-5-(((tert-butyldiphenyl)silyl)oxy)hexahydro[1,3]benzodioxol-4-carbonyl]bornane-10,2-sultam 
• 934831-77-3 (+)-(2S)-N-[(1R,2R,3S,4R)-1-(((tert-butyldiphenyl)silyl)oxy)-3,4-(dihydroxy)cyclohexane-2-carbonyl]bornane-10,2-sultam 
• 934831-76-2 (+)-(2S)-N-[(1R,2S)-1-(((tert-butyldiphenyl)silyl)oxy)-3-cyclohexene-2-carbonyl]bornane-10,2-sultam 
• 934831-74-0 (+)-(2S)-N-[(1R,2S)-1-hydroxy-3-cyclohexene-2-carbonyl]bornane-10,2-sultam 
• 606933-61-3 (-)-N-[(1'R,6'R)-6-methyl-3-cyclohexenylcarbonyl]bornane-10,2-sultam 
• 221665-01-6 (3S,4S)-4-tert-butoxycarbonyl-3-ethyl-1-(4-methoxyphenyl)azetidin-2-one 
• 117901-09-4 (2S,3R)-3-Ethyl-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid tert-butyl ester 

Relevant articles and documents

A Total Synthesis of Salinosporamide A

Salinosporamide A is a β-lactone proteasome inhibitor currently in clinical trials for the treatment of multiple-myeloma. Herein we report a short synthesis of this small, highly functionalized, biologically important natural product that uses an oxidative radical cyclization as a key step and allows for the preparation of gram quantities of advanced synthetic intermediates.

Syntheses of isotopically labelled L-?±-amino acids with an asymmetric centre at C-3

Approaches are described to the synthesis of a series of isotopically labelled L-a-amino acids each with an asymmetric centre at C-3, including isoleucine, allo-isoleucine, threonine and allo-threonine. The methods may be simply adapted for the selective incorporation of an isotopic label at each site of L-valine including the selective labelling of either diastereotopic methyl group with carbon-13 and/or deuterium and labelling of the amine with nitrogen-15. ? The Royal Society of Chemistry 2000.

Ruthenium catalyzed asymmetric dihydroxylation with sultams as chiral auxiliaries

Ruthenium catalyzed asymmetric dihydroxylations of α,β-unsaturated carbonyl compounds with sultams 4, 5 and 6 as chiral auxiliaries are reported.