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HomeProduct name list(2R)-Bornane-10,2-sultam

(2R)-Bornane-10,2-sultam

Synonym(s):(−)-10,2-Camphorsultam;(−)-exo-10,2-Bornanesultam;(1S,5R)-10,10-Dimethyl-3-thia-4-azatricyclo[5.2.1.01,5]decane 3,3-dioxide;[3aS-(3aα,6α,7aβ)]-hexahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazole-2,2-dioxide

(2R)-Bornane-10,2-sultam Structural

What is (2R)-Bornane-10,2-sultam?

Chemical properties

white to light yellow crystal powde

The Uses of (2R)-Bornane-10,2-sultam

(2R)-Bornane-10,2-sultam is a reagent used to make Camphorsultam conjugates.

The Uses of (2R)-Bornane-10,2-sultam

(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.

The Uses of (2R)-Bornane-10,2-sultam

(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.

General Description

(1S,2R,4R)-(?)-2,10-Camphorsultam may be employed as a chiral probe for the optical resolution by HPLC and X-ray crystallographic determination of the absolute stereochemistry of carboxylic acids.

Purification Methods

The (-)-enantiomer is recrystallised from 95% EtOH and dried in a vacuum desiccator. It dissolves in dilute aqueous NaOH and can be precipitated without hydrolysis by acidifying. It forms the N-Na salt in EtOH (by addition of Na to the EtOH solution), and the salt can be methylated with MeI to give the (-)-N-Me lactam with m 80o after recrystallisation from hot H2O and has []D -59.6o (c 5, CHCl3) [Shriner et al. J Am Chem Soc 60 2794 1938]. [Oppolzer et al. Helv Chim Acta 69 1142 1986, Weismiller et al. Org Synth 69 154 1955, Beilstein 27 III/IV 1007.]

Properties of (2R)-Bornane-10,2-sultam

Melting point: 183-185 °C
Boiling point: 324.8±25.0 °C(Predicted)
alpha  -33 º (c=4.9, CHCl3)
Density  1.1469 (rough estimate)
refractive index  -31 ° (C=1, CHCl3)
storage temp.  Sealed in dry,Room Temperature
solubility  Chloroform, Ethanol, Methanol
form  Liquid
pka 11.05±0.40(Predicted)
color  Clear colorless
optical activity [α]19/D 32°, c = 5 in chloroform
Water Solubility  Slightly soluble in water.
BRN  83811
CAS DataBase Reference 94594-90-8(CAS DataBase Reference)
NIST Chemistry Reference (-)-10,2-Camphorsultam(94594-90-8)

Safety information for (2R)-Bornane-10,2-sultam

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for (2R)-Bornane-10,2-sultam

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