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345350 Sigma-Aldrich

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

Synonym: (1S)-(+)-(Camphorylsulfonyl)oxaziridine, (1S)-(+)-2,N-Epoxy-exo-10,2-bornanesultam

  • CAS Number 104322-63-6

  • Empirical Formula (Hill Notation) C10H15NO3S

  • Molecular Weight 229.30

  •  Beilstein/REAXYS Number 6274370

  •  MDL number MFCD21332910

  •  PubChem Substance ID 24861312

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Hydroxylation
Quality Level   200
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.

Packaging

1 g in glass bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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