345350

(1S)-(+)-(10-Camphorsulfonyl)oxaziridine

• Synonym(s): (1S)-(+)-(Camphorylsulfonyl)oxaziridine, (1S)-(+)-2,N-Epoxy-exo-10,2-bornanesultam
• Empirical Formula (Hill Notation): C₁₀H₁₅NO₃S
• CAS Number: 104322-63-6
• Molecular Weight: 229.30
• Beilstein/REAXYS Number: 6274370
• MDL number: MFCD21332910
• UNSPSC Code: 12352005
• PubChem Substance ID: 24861312
• NACRES: NA.22

Properties

• form: solid
• optical activity: [α]28/D +45°, c = 2 in chloroform
• impurities: <1% toluene
• mp: 172-174 °C (lit.)
• storage temp.: 2-8°C
• SMILES string: CC1(C)[C@@H]2CC[C@]13CS(=O)(=O)N4O[C@@]34C2
• InChI: 1S/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?/m1/s1
• InChI key: GBBJBUGPGFNISJ-YDQXZVTASA-N

Description

Application

(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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)