CAS 104322-63-6 (1S)-(10-Camphorsulfonyl)oxaziridine

Synonyms

1alpha,7aalpha-Epoxy-3abeta,6beta-isopropylideneoctahydro-2,1-benzoisothiazole 2,2-dioxide; (+)-((CAMPHORYL)SULFONYL)OXAZIRIDINE; (1S)-(+)-2,N-Epoxy-exo-10,2-bornanesultam; ZINC4202596; (camphorylsul-fonyl)oxaziridine; camphor-sulfonyloxaziridine; (1S)-(+)-(10-Camphorsulfonyl)oxaziridine; (+)-(2r,8as)-(camphorsulfonyl)oxaziridine; (4aS,7R,8aS)-9,9-Dimethyltetrahydro-4H-4a,7-methanobenzo[c][1,2]oxazireno[2,3-b]isothiazole 3,3-dioxide; GBBJBUGPGFNISJ-YDQXZVTASA-N;

IUPAC Name

(1S,6S,8R)-11,11-dimethyl-5-oxa-3λ6-thia-4-azatetracyclo[6.2.1.01,6.04,6]undecane 3,3-dioxide;

Molecular Weight

229.294g/mol

Molecular Formula

C10H15NO3S;

Canonical SMILES

CC1(C2CCC13CS(=O)(=O)N4C3(C2)O4)C;

InChI

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;

Storage

2-8°C

Complexity

466

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

Exact Mass

229.077g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

229.077g/mol

Topological Polar Surface Area

58.1A^2

Application

(1S)-(10-Camphorsulfonyl)oxaziridine is a versatile synthetic intermediate, presented as a white crystalline powder, that serves multiple purposes in organic synthesis. It plays a crucial role in the enantioselective asymmetric oxidation of prochiral ketone enolates to yield optically active α-hydroxy ketones. Additionally, it facilitates the creation of thymidine oligonucleotides linked through pyrophosphates and contributes significantly to the asymmetric synthesis of proton pump inhibitors, such as (R)-Rabeprazole sodium and (R)-Lansoprazole sodium, from the DBU salt of prochiral sulfides. Furthermore, this compound is instrumental in the preparation of phosphonoacetate and thiophosphonoacetate oligodeoxynucleotides through the oxidation of the corresponding phosphinoacetate, making it a critical component in various synthetic applications.

March 25, 2025

Highly Effective Oxidation Agent for Asymmetric Synthesis

I've been using (1S)-(10-Camphorsulfonyl)oxaziridine from Alfa Chemistry in our research to achieve enantioselective oxidations. This white crystalline powder consistently enhances our synthesis process, especially for optically active α-hydroxy ketones and proton pump inhibitors.