(1S)-(+)-(Camphorylsulfonyl)oxaziridine CAS 104322-63-6

Introduction：Basic information about (1S)-(+)-(Camphorylsulfonyl)oxaziridine CAS 104322-63-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

(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
• 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 Information

• 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.