679712
S-Methyl N-(2,2,2-trichloroethoxysulfonyl)carbonchloroimidothioate
97%
Synonym(s):
N-(2,2,2-Trichloroethoxysulfonyl)carbonchlorothioic acid S methyl ester
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About This Item
Empirical Formula (Hill Notation):
C4H5Cl4NO3S2
CAS Number:
Molecular Weight:
321.03
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352101
MDL number:
Assay:
97%
Form:
solid
form
solid
InChI
1S/C4H5Cl4NO3S2/c1-13-3(5)9-14(10,11)12-2-4(6,7)8/h2H2,1H3/b9-3+
SMILES string
CS\C(Cl)=N\S(=O)(=O)OCC(Cl)(Cl)Cl
InChI key
NGCLYHLLOXVGSU-YCRREMRBSA-N
assay
97%
mp
75-79 °C
functional group
chloro, thioether
Application
Reactant for preparation of:
- Muramycin analogs as antibacterial agents against drug-resistant bacteria
- L-epicapreomycidine using rhodium-catalyzed stereoselective oxidative cyclization
- (+)-gonyautoxin 3 via Rh-catalyzed amination
- (+)-monobromophakellin and (+)-phakellin via a strategy applicable to synthesis of more complex members of this family of marine sponge-derived alkaloids including palau′amine
- 2-imidazolidinones and 2-imino-1,3-imidazolidines
Reagent for preparation of protected guanidine derivatives.
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Mihyong Kim et al.
Organic letters, 8(6), 1073-1076 (2006-03-10)
[reaction: see text] Oxidative C-H amination of N-trichloroethoxysulfonyl-protected ureas and guanidines is demonstrated to proceed in high yield for tertiary and benzylic-derived substrates. The success of these reactions is predicated on the choice of the electron-withdrawn 2,2,2-trichloroethoxysulfonyl (Tces) protecting group
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