ChemicalBook > CAS DataBase List > (1R)-(-)-(10-Camphorsulfonyl)oxaziridine
(1R)-(-)-(10-Camphorsulfonyl)oxaziridine
(1R)-(-)-(10-Camphorsulfonyl)oxaziridine
- CAS No.104372-31-8
- Chemical Name:(1R)-(-)-(10-Camphorsulfonyl)oxaziridine
- CBNumber:CB9768000
- Molecular Formula:C10H15NO3S
- Formula Weight:229.3
- MOL File:104372-31-8.mol
(1R)-(-)-(10-Camphorsulfonyl)oxaziridine Property
- Melting point 170-174 °C
- Boiling point 317.6±25.0 °C(Predicted)
- alpha -46.6 º (c=2, CHCl3 25 ºC)
- Density 1.2486 (rough estimate)
- refractive index 1.5060 (estimate)
- Flash point 170℃
- storage temp. 2-8°C
- solubility Chloroform (Slightly), Methanol (Slightly)
- pka -11.75±0.40(Predicted)
- form Powder
- color White
- optical activity [α]20/D 44°, c = 2.2 in chloroform
- BRN 6274369
- CAS DataBase Reference 104372-31-8(CAS DataBase Reference)
- UNSPSC Code 12352005
- NACRES NA.22
Safety
- Hazard Codes :Xi
- Risk Statements :36/37/38
- Safety Statements :26-36-24/25
- WGK Germany :3
- F :10
- HS Code :29349990
-
NFPA 704:
1 0 0
-
Symbol(GHS)
- Signal wordWarning
- Hazard statements H302-H315-H319-H335
- Precautionary statements P261-P280-P301+P312-P302+P352-P305+P351+P338
(1R)-(-)-(10-Camphorsulfonyl)oxaziridine Price
More Price(4)
- Brand: Sigma-Aldrich
- Product number: 349003
- Product name : (1R)-(−)-(10-Camphorsulfonyl)oxaziridine
- Purity:
- Packaging: 1G
- Price: ₹8350
- Updated: 2022/06/14
- Buy: Buy
- Brand: Sigma-Aldrich(India)
- Product number: 349003
- Product name : (1R)-(−)-(10-Camphorsulfonyl)oxaziridine
- Purity:
- Packaging: 1G
- Price: ₹8350
- Updated: 2022/06/14
- Buy: Buy
- Brand: TCI Chemicals (India)
- Product number: C1327
- Product name : (2S,8aR)-(-)-(Camphorylsulfonyl)oxaziridine [Asymmetric Oxidizing Reagent]
- Purity:
- Packaging: 1G
- Price: ₹6200
- Updated: 2022/05/26
- Buy: Buy
- Brand: TCI Chemicals (India)
- Product number: C1327
- Product name : (2S,8aR)-(-)-(Camphorylsulfonyl)oxaziridine [Asymmetric Oxidizing Reagent]
- Purity:
- Packaging: 5G
- Price: ₹14500
- Updated: 2022/05/26
- Buy: Buy
(1R)-(-)-(10-Camphorsulfonyl)oxaziridine Chemical Properties,Usage,Production
- Chemical Properties White crystalline powder
-
Uses
Reactant involved in:
- Asymmetric synthesis of proton pump inhibitors
- Asymmetric synthesis of polyhydroxylated pyrrolidines
- Diastereoselective hydroxylation of chlorophylls a and b enolate anions
Used in impregnated silica nanoparticles for removal of sulfur mustard from wastewater
Used to modify blebbistatin for investigations of myosin inhibitor design - Uses (1R)-(-)-(10-Camphorsulfonyl)oxaziridine is a useful synthetic intermediate. Used for asymmetric hydroxylation.
-
Synthesis
The enantiopure (1S)-(+)-(Camphorylsulfonyl)oxaziridine and (1R)-(-)-(10-Camphorsulfonyl)oxaziridine and [(8,8- dichlorocamphor)sulfonyl]oxaziridines (2) are commercially available. They can also be prepared on a large scale via the oxidation of corresponding camphorsulfonimines with buffered Potassium Monoperoxysulfate (Oxone) or buffered peracetic acid. Since oxidation takes place from the endo face of the C=N double bond, only a single oxaziridine isomer is obtained. The precursor camphorsulfonimines can be prepared in 3 steps (>80% yield) from inexpensive (+)- and (-)-10-Camphorsulfonic Acids. A variety of (camphorylsulfonyl)oxaziridine derivatives such as (2)-(4) are also readily available via the functionalization of the camphorsulfonimines followed by oxidation.
- Synthesis (1R)-(-)-(10-Camphorsulfonyl)oxaziridine is a neutral, aprotic, electrophilic, and asymmetric oxidizing agents for the chemoselective oxidation of many nucleophilic substrates such as sulfides, enamines, enol esters, carbanions, and enolates.
-
References
1. Mergelsberg, I.; Gala, D.; Scherer, D.; DiBenedetto, D.; Tanner TL 1992, 33, 161.
2. Davis, F. A.; Kumar, A.; Chen, B.-C. JOC 1991, 56, 1143.
3. Chen, B.-C.; Weismiller, M. C.; Davis, F. A.; Boschelli, D.; Empfield, J. R.; Smith, III, A. B. T 1991, 47, 173.
(1R)-(-)-(10-Camphorsulfonyl)oxaziridine Preparation Products And Raw materials
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