(1R)-(+)-2,10-Camphorsultam

Base Information

• Chemical Name: (1R)-(+)-2,10-Camphorsultam
• CAS No.: 94594-90-8
• Molecular Formula: C10H17NO2S
• Molecular Weight: 215.316
• Hs Code.: 29349990
• European Community (EC) Number: 626-448-2,628-426-8
• DSSTox Substance ID: DTXSID40910735
• Nikkaji Number: J382.973A,J734.685I
• Wikidata: Q15410857,Q72451077
• Mol file: 94594-90-8.mol

Synonyms:108448-77-7;(2S)-Bornane-10,2-sultam;(+)-10,2-Camphorsultam;(1R)-(+)-2,10-Camphorsultam;MFCD00151762;(3aR,6S,7aS)-8,8-Dimethylhexahydro-1H-3a,6-methanobenzo[c]isothiazole 2,2-dioxide;(1R)-(+)-2,10,Camphorsultam;L-2,10-Camphorsultam;(+)-exo-10,2-Bornanesultam;94594-90-8;(1R)-(+)-Camphorsultam;SCHEMBL4147091;DTXSID40910735;DPJYJNYYDJOJNO-NRPADANISA-N;BCP06365;FD1226;(+)-10,2-CAMPHORSULTAM?;AKOS016842377;CS-W002434;(1R,2S)-(+)-10,2-Camphorsultam;(1R,5S)-10,10-Dimethyl-3-thia-4-azatricyclo[5.2.1.01,5]decane 3,3-dioxide;(1R)-(+)-2,10-Camphorsultam, 98%;AM20120715;EN300-1177730;Q15410857;(1R,5S,7S)-10,10-dimethyl-3lambda6-thia-4-azatricyclo[5.2.1.0,1,5]decane-3,3-dione;1932472-17-7;3H-3a,6-Methano-2,1-benzisothiazole, hexahydro-8,8-dimethyl-, 2,2-dioxide, (3aR,6S,7aS)-

Chemical Property of (1R)-(+)-2,10-Camphorsultam

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.000239mmHg at 25°C
• Melting Point: 183-185 °C
• Refractive Index: -31 ° (C=1, CHCl3)
• Boiling Point: 324.8 °C at 760 mmHg
• PKA: 11.05±0.40(Predicted)
• Flash Point: 150.3 °C
• PSA: 54.55000
• Density: 1.193 g/cm³
• LogP: 2.52390
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Ethanol, Methanol
• Water Solubility.: Slightly soluble in water.
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 215.09799996
• Heavy Atom Count: 14
• Complexity: 381

Purity/Quality:

99% ^*data from raw suppliers

(1S)-Camphorsultam ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC13CS(=O)(=O)NC3C2)C
• Isomeric SMILES: CC1([C@H]2CC[C@@]13CS(=O)(=O)N[C@H]3C2)C
• Uses: (2R)-Bornane-10,2-sultam is a reagent used to make Camphorsultam conjugates. (1S,2R)-(-)-10,2-Camphorsultam is used in the asymmetric synthesis of (S)- and (R)-N-Fmoc-S-trityl-α-methylcysteine. It is used as proton source in the synthesis of chiral α,γ-substituted γ-butyrolactones. It is also employed as a chiral probe for the optical resolution by HPLC and X-ray crystallographic determination of the absolute stereochemistry of carboxylic acids. Also used to prepare N-acryloyl derivatives which are employed as dienophiles in asymmetric Diels-Alder reactions. and for other asymmetric transformations. (1S)-(?)-2,10-Camphorsultam may be used in the asymmetric synthesis of (S)- and (R)-N-Fmoc-S-trityl-α-methylcysteine. It may be used as proton source in the synthesis of chiral α,γ-substituted γ-butyrolactones.

Technology Process of (1R)-(+)-2,10-Camphorsultam

There total 129 articles about (1R)-(+)-2,10-Camphorsultam 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: 98.0%

C26H37NO5S → C16H22O3 (1422463-22-6) + (2R)-bornane-10,2-sultam (94594-90-8,124224-04-0)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jo3026077

Reference yield: 98.0%

(2R,2'S)-N-phenylalanyl>bornane-10,2-sultam + allyl alcohol (107-18-6) → (2S)-N-<(fluoren-9-yl)methoxycarbonyl>phenylalanine prop-2-enyl ester (146549-19-1) + (2R)-bornane-10,2-sultam (94594-90-8,124224-04-0)

Guidance literature:

With titanium(IV) tetraethanolate; at 130 ℃; for 1h;

DOI:10.1002/hlca.19920750812

Reference yield: 95.0%

(R)-2-amino-3-cyano-6-methyl-5-(N-oxobornane-10,2-sultam)-4-phenyl-4H-pyran (153897-28-0) → 2-amino-3-cyano-5-hydroxymethyl-6-methyl-4-phenyl-4H-pyran + (2R)-bornane-10,2-sultam (94594-90-8,124224-04-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 3h;

DOI:10.1016/S0040-4020(01)87029-0

upstream raw materials:

(1S)-(-)-camphorsulfonylimine

diazomethane

N-<(2R,3S)-3-hydroxy-2-methylbutanoyl>bornane-10,2-sultam

N-<(2R,3S)-3-hydroxy-2,4-dimethylpentanoyl>bornane-10,2-sultam

Downstream raw materials:

(1S)-N-crotyl-2,10-camphorsultam

acrylcamphorsultam

(3aS,6R,7aR)-1-(cyclohex-1-en-1-ylcarbonyl)-8,8-dimethylhexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide

4-[(E)-3-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-oxo-propenyl]-benzonitrile

Refernces

• 1、 Zhang, Lumin,Zhu, Lili,Yang, Jun,Luo, Jisheng,Hong, Ran. "Stereoselective α-Hydroxylation of Amides Using Oppolzer's Sultam as Chiral Auxiliary". . p. 3890 - 3900. Retrieved 2016/05/24.
• 2、 Johnston, Heather J.,Hulme, Alison N.. "A facile, inexpensive and scalable route to thiol-protected α-methyl cysteine". supporting information. p. 591 - 594. Retrieved 2013/04/10.