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345350

Sigma-Aldrich

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

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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:
6274370
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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

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1 of 4

This Item
34900335603U111
optical activity

[α]28/D +45°, c = 2 in chloroform

optical activity

[α]20/D −44°, c = 2.2 in chloroform

optical activity

[α]20/D +89±3°, c = 0.5% in chloroform

optical activity

[α]22/D -39.0 to -32.0°, c = 0.5 in methanol(lit.)

mp

172-174 °C (lit.)

mp

-

mp

-

mp

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

Quality Level

200

Quality Level

-

Quality Level

100

Quality Level

100

impurities

<1% toluene

impurities

-

impurities

-

impurities

-

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Customers Also Viewed

Slide 1 of 3

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On the synthesis of oligonucleotides interconnected through pyrophosphate linkages
Kistemaker HAV, et al.
European Journal of Organic Chemistry, 2015(27), 6084-6091 (2015)
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)
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)
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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