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298352

(1S)-(−)-2,10-Camphorsultam

Name: (1<I>S</I>)-(−)-2,10-Camphorsultam
Brand: ALDRICH

98%

Sinónimos:

(−)-10,2-Camphorsultam, (−)-exo-10,2-Bornanesultam, (1S,5R)-10,10-Dimethyl-3-thia-4-azatricyclo[5.2.1.0^1,5]decane 3,3-dioxide, [3aS-(3aα,6α,7aβ)]-hexahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazole-2,2-dioxide

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About This Item

Fórmula empírica (notación de Hill):

C₁₀H₁₇NO₂S

Número de CAS:

94594-90-8

Peso molecular:

215.31

Beilstein/REAXYS Number:

83811

MDL number:

MFCD00066271

UNSPSC Code:

12352005

PubChem Substance ID:

24857980

NACRES:

NA.22

assay

98%

form

solid

optical activity

[α]19/D −32°, c = 5 in chloroform

mp

181-183 °C (lit.)

SMILES string

[H][C@@]12CC[C@]3(CS(=O)(=O)N[C@@H]3C1)C2(C)C

InChI

1S/C10H17NO2S/c1-9(2)7-3-4-10(9)6-14(12,13)11-8(10)5-7/h7-8,11H,3-6H2,1-2H3/t7-,8-,10-/m1/s1

InChI key

DPJYJNYYDJOJNO-NQMVMOMDSA-N

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.

Application

(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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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A chiral probe useful for optical resolution and X-ray crystallographic determination of the absolute stereochemistry of carboxylic acids.

Harada N, et al.

Tetrahedron Asymmetry, 4(8), 1755-1758 (1993)

Development of a new reaction system for the synthesis of highly optically active alpha,gamma-substituted gamma-butyrolactones.

M H Xu et al.

The Journal of organic chemistry, 66(11), 3953-3962 (2001-05-26)

A highly useful method for the synthesis of optically active alpha,gamma-substituted gamma-butyrolactones has been developed. The SmI(2)-induced reductive coupling of chiral 2-alkyl acrylates derived from isosorbide with ketones in the presence of (1S)-(-)-2,10-camphorsultam as a proton source give the chiral

Efficient asymmetric synthesis of (S)- and (R)-N-Fmoc-S-trityl-alpha-methylcysteine using camphorsultam as a chiral auxiliary.

Satendra Singh et al.

The Journal of organic chemistry, 69(13), 4551-4554 (2004-06-19)

(1R)-(+)-2,10- and (1S)-(-)-2,10-camphorsultam were acylated with ethyl 2-phenylthiazoline 4-carboxylate to afford (+)- and (-)-2-phenylthiazolinylcamphorsultam, which were stereoselectively alkylated with MeI in the presence of n-BuLi. Alkylation of these phenylthiazolinylcamphorsultams occurred from the beta-face rather than alpha-face, resulting in the formation

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