(1S)-(+)-(Camphorylsulfonyl)oxaziridine

Bezeichnung:(1S)-(+)-(Camphorylsulfonyl)oxaziridine

CAS-Nr104322-63-6

Englisch Name:(1S)-(+)-(Camphorylsulfonyl)oxaziridine

CBNumberCB3447891

SummenformelC10H15NO3S

Molgewicht229.3

MOL-Datei104322-63-6.mol

(1S)-(+)-(Camphorylsulfonyl)oxaziridine physikalisch-chemischer Eigenschaften

Schmelzpunkt	172-174 °C(lit.)
alpha	45 º (c=2, chloroform)
Siedepunkt	317.6±25.0 °C(Predicted)
Dichte	1.2486 (rough estimate)
Brechungsindex	1.5060 (estimate)
storage temp.	2-8°C
Löslichkeit	Chloroform (Sparingly), Methanol (Slightly)
pka	-11.75±0.40(Predicted)
Aggregatzustand	Crystals or Crystalline Powder
Farbe	White
Optische Aktivität	[α]28/D +45°, c = 2 in chloroform
BRN	6274370
CAS Datenbank	104322-63-6(CAS DataBase Reference)

Sicherheit

S-Sätze:	22-24/25
WGK Germany	3
F	10
HS Code	29309090

Gefahreninformationscode (GHS)

(1S)-(+)-(Camphorylsulfonyl)oxaziridine Chemische Eigenschaften,Einsatz,Produktion Methoden

S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Chemische Eigenschaften
(1S)-(+)-(Camphorylsulfonyl)oxaziridine is white crystall powder
Verwenden
(1S)-(+)-(Camphorylsulfonyl)oxaziridine is a useful synthetic intermediate. Used for asymmetric hydroxylation
Verwenden
(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.
Definition
(1S)-(+)-(Camphorylsulfonyl)oxaziridine is a neutral, aprotic, electrophilic, and asymmetric oxidizing agents for the chemoselective oxidation of many nucleophilic substrates such as sulfides, enamines, enol esters, carbanions, and enolates.
Synthese
The enantiopure (1S)-(+)-(Camphorylsulfonyl)oxaziridine and (1R)-(-)-(10-Camphorsulfonyl)oxaziridine and [(8,8- dichlorocamphor)sulfonyl]oxaziridines (2) are commercially available. They can also be prepared on a large scale via the oxidation of corresponding camphorsulfonimines with buffered Potassium Monoperoxysulfate (Oxone) or buffered peracetic acid. Since oxidation takes place from the endo face of the C=N double bond, only a single oxaziridine isomer is obtained. The precursor camphorsulfonimines can be prepared in 3 steps (>80% yield) from inexpensive (+)- and (-)-10-Camphorsulfonic Acids. A variety of (camphorylsulfonyl)oxaziridine derivatives such as (2)-(4) are also readily available via the functionalization of the camphorsulfonimines followed by oxidation.
Einzelnachweise
1. Mergelsberg, I.; Gala, D.; Scherer, D.; DiBenedetto, D.; Tanner TL 1992, 33, 161.
2. Davis, F. A.; Kumar, A.; Chen, B.-C. JOC 1991, 56, 1143.
3. Chen, B.-C.; Weismiller, M. C.; Davis, F. A.; Boschelli, D.; Empfield, J. R.; Smith, III, A. B. T 1991, 47, 173.

(1S)-(+)-(Camphorylsulfonyl)oxaziridine Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

104322-63-6, (1S)-(+)-(Camphorylsulfonyl)oxaziridine Verwandte Suche:

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