345350

Sigma-Aldrich

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

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

Quality Level

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

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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

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

On the synthesis of oligonucleotides interconnected through pyrophosphate linkages
Kistemaker HAV, et al.
European Journal of Organic Chemistry, 2015(27), 6084-6091 (2015)
Davis oxaziridine-mediated asymmetric synthesis of proton pump inhibitors using DBU salt of prochiral sulfide
Mahale RD, et al.
Organic Process Research & Development, 14(5), 1264-1268 (2010)
Chemistry of oxaziridines. 14. Asymmetric oxidation of ketone enolates using enantiomerically pure (camphorylsulfonyl) oxaziridine
Davis FA, et al.
Journal of the American Chemical Society, 112(18), 6679-6690 (1990)
Douglas J Dellinger et al.
Journal of the American Chemical Society, 125(4), 940-950 (2003-01-23)
Phosphonoacetate and thiophosphonoacetate oligodeoxynucleotides were prepared via a solid-phase synthesis strategy. Under Reformatsky reaction conditions, novel esterified acetic acid phosphinodiamidites were synthesized and condensed with appropriately protected 5'-O-(4, 4'-dimethoxytrityl)-2'-deoxynucleosides to yield 3'-O-phosphinoamidite reactive monomers. These synthons when activated with tetrazole...

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