(1S,8S)-11,11-dimethyl-5-oxa-3lambda6-thia-4-azatetracyclo[6.2.1.01,6.04,6]undecane 3,3-dioxide

Base Information

• Chemical Name: (1S,8S)-11,11-dimethyl-5-oxa-3lambda6-thia-4-azatetracyclo[6.2.1.01,6.04,6]undecane 3,3-dioxide
• CAS No.: 104322-63-6
• Molecular Formula: C₁₀H₁₅NO₃S
• Molecular Weight: 229.3
• Hs Code.: 29309090
• European Community (EC) Number: 814-455-5
• Mol file: 104322-63-6.mol

Synonyms:(1S)-(+)-(10-Camphorsulfonyl)oxaziridine;104322-63-6;(2R,8aS)-(+)-(Camphorylsulfonyl)oxaziridine;GBBJBUGPGFNISJ-INKAGXRRSA-N;(1S)-(+)-(10-camphorsulfonyl)-oxaziridine;(2r,8as)-(+)-(camphorylsulphonyl)-oxaziridine;(1S,8S)-11,11-dimethyl-5-oxa-3lambda6-thia-4-azatetracyclo[6.2.1.01,6.04,6]undecane 3,3-dioxide;(4aS,7S)-9,9-Dimethyltetrahydro-4H-4a,7-methanobenzo[c][1,2]oxazireno[2,3-b]isothiazole 3,3-dioxide;1217495-71-0

Chemical Property of (1S,8S)-11,11-dimethyl-5-oxa-3lambda6-thia-4-azatetracyclo[6.2.1.01,6.04,6]undecane 3,3-dioxide

Chemical Property:

• Appearance/Colour: white crystall powder
• Vapor Pressure: 0.000381mmHg at 25°C
• Melting Point: 172-174 °C
• Refractive Index: 1.63
• Boiling Point: 317.6 °C at 760 mmHg
• PKA: -11.75±0.40(Predicted)
• Flash Point: 145.9 °C
• PSA: 58.06000
• Density: 1.49 g/cm³
• LogP: 2.11830
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 229.07726451
• Heavy Atom Count: 15
• Complexity: 466

Purity/Quality:

99% ^*data from raw suppliers

(1S)-(+)-(10-Camphorsulfonyl)oxaziridine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC13CS(=O)(=O)N4C3(C2)O4)C
• Isomeric SMILES: CC1([C@H]2CC[C@]13CS(=O)(=O)N4C3(C2)O4)C
• Uses: (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. (1S)-(+)-(Camphorylsulfonyl)oxaziridine is a useful synthetic intermediate. Used for asymmetric hydroxylation

Technology Process of (1S,8S)-11,11-dimethyl-5-oxa-3lambda6-thia-4-azatetracyclo[6.2.1.01,6.04,6]undecane 3,3-dioxide

There total 6 articles about (1S,8S)-11,11-dimethyl-5-oxa-3lambda6-thia-4-azatetracyclo[6.2.1.01,6.04,6]undecane 3,3-dioxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

(1S)-(-)-camphorsulfonylimine (60886-80-8) → (2R,4aS,7R,8aS)-tetrahydro-9,9-dimethyl-4H-4a,7-methanooxazirino<3,2-i><2,1>benzoisothiazole 3,3-dioxide (104322-63-6,104372-31-8)

Guidance literature:

With Oxone; 18-crown-6 ether; sodium hydrogencarbonate; for 120h;

DOI:10.1021/jo00362a053

Reference yield: 93.0%

(+)-(camphorylsulfonyl)imine (107869-45-4) → C10H15NO3S (104322-63-6,104372-31-8)

Guidance literature:

With Oxone; 18-crown-6 ether; sodium hydrogencarbonate; for 120h;

DOI:10.1021/jo00362a053

Reference yield:

(1S)-(-)-camphorsulfonylimine (60886-80-8) → (+)-(2R,8aS)-(camphorylsulfonyl)oxaziridine (104322-63-6)

Guidance literature:

With Oxone; potassium carbonate; In water; toluene; Yield given; Ambient temperature;

DOI:10.1021/ja00233a025

upstream raw materials:

(+)-(camphorylsulfonyl)imine

(1S)-(-)-camphorsulfonylimine

Camphorsulfonyl chloride

(1S)-10-camphorsulfonamide

Refernces

• 1、 Davis,F.A.,Towson,J.C.,Weismiller,M.C.. "-". . p. 8477. Retrieved 1988.