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| | (1S)-(+)-(Camphorylsulfonyl)oxaziridine Basic information |
| Product Name: | (1S)-(+)-(Camphorylsulfonyl)oxaziridine | | Synonyms: | (2R,8AS)-(+)-(CAMPHORYLSULFONYL)OXAZIRIDINE;(1S)-(+)-2,N-EPOXY-EXO-10,2-BORNANESULTAM;(IS)-(+)-(10-Camphorsulfonyl)oxaziridine;S-(10-Camphorsulfonyl)oxaziridine;(4aS,7R,8aS)-9,9-DiMethyltetrahydro-4H-4a,7-Methanobenzo[c][1,2]oxazireno[2,3-b]isothiazole 3,3-dioxide;(+)-(2R,8aS)-10-(CaMphorylsulfonyl)oxaziridine;(4aS,7R,8aS)-Tetrahydro-9,9-diMethyl-4H-4a,7-Methanooxazirino[3,2-i][2,1]benzisothiazole 3,3-Dioxide;(1S)-(+)-(Camphorylsulfonyl)oxaziridine, (1S)-(+)-2,N-Epoxy-exo-10,2-bornanesultam | | CAS: | 104322-63-6 | | MF: | C10H15NO3S | | MW: | 229.3 | | EINECS: | | | Product Categories: | Intermediates & Fine Chemicals;Pharmaceuticals;Chiral Reagents;pharmacetical;chiral;Asymmetric Synthesis;Bicyclic Monoterpenes;Biochemistry;Oxidation;Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;Terpenes | | Mol File: | 104322-63-6.mol |  |
| | (1S)-(+)-(Camphorylsulfonyl)oxaziridine Chemical Properties |
| Melting point | 172-174 °C(lit.) | | alpha | 45 º (c=2, chloroform) | | Boiling point | 317.6±25.0 °C(Predicted) | | density | 1.2486 (rough estimate) | | refractive index | 1.5060 (estimate) | | storage temp. | 2-8°C | | solubility | Chloroform (Sparingly), Methanol (Slightly) | | pka | -11.75±0.40(Predicted) | | form | Crystals or Crystalline Powder | | color | White | | Optical Rotation | [α]28/D +45°, c = 2 in chloroform | | BRN | 6274370 | | InChI | InChI=1/C10H15NO3S/c1-8(2)7-3-4-9(8)6-15(12,13)11-10(9,5-7)14-11/h7H,3-6H2,1-2H3/t7-,9-,10,11/s3 | | InChIKey | GBBJBUGPGFNISJ-SENRVMEJNA-N | | SMILES | C123C[C@]4([H])CC[C@@]1(C4(C)C)CS(=O)(=O)N2O3 |&1:2,6,r| | | CAS DataBase Reference | 104322-63-6(CAS DataBase Reference) |
| Safety Statements | 22-24/25 | | WGK Germany | 3 | | F | 10 | | HS Code | 29309090 | | Storage Class | 11 - Combustible Solids |
| | (1S)-(+)-(Camphorylsulfonyl)oxaziridine Usage And Synthesis |
| Chemical Properties | (1S)-(+)-(Camphorylsulfonyl)oxaziridine is white crystall powder | | Uses | (1S)-(+)-(10-Camphorsulfonyl)oxaziridine can be used:
- To convert prochiral ketone enolates into optically active α-hydroxy ketones via enantioselective asymmetric oxidation.
- In the synthesis of thymidine oligonucleotides connected through pyrophosphates.
- In the asymmetric synthesis of proton pump inhibitors like (R)-Rabeprazole sodium and (R)-Lansoprazole sodium from the corresponding DBU salt of prochiral sulfide.
- In the preparation of phosphonoacetate and thiophosphonoacetate oligodeoxynucleotides by oxidizing the corresponding phosphinoacetate.
| | Uses | (1S)-(+)-(Camphorylsulfonyl)oxaziridine is a useful synthetic intermediate. Used for asymmetric hydroxylation | | Definition | (1S)-(+)-(Camphorylsulfonyl)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.
| | 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.
 | | 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. |
| | (1S)-(+)-(Camphorylsulfonyl)oxaziridine Preparation Products And Raw materials |
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