2,2,2-Trichloroacetamide
2,2,2-Trichloroacetamide structure
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Common Name | 2,2,2-Trichloroacetamide | ||
|---|---|---|---|---|
| CAS Number | 594-65-0 | Molecular Weight | 162.402 | |
| Density | 1.7±0.1 g/cm3 | Boiling Point | 239.0±0.0 °C at 760 mmHg | |
| Molecular Formula | C2H2Cl3NO | Melting Point | 139-141 °C(lit.) | |
| MSDS | USA | Flash Point | 88.5±25.9 °C | |
| Symbol |
GHS07 |
Signal Word | Warning | |
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An improved synthesis of (-)-5,11-dideoxytetrodotoxin.
J. Org. Chem. 78(4) , 1699-705, (2013) We describe an improved synthesis of (-)-5,11-dideoxytetrodotoxin from an enone, which was used for synthesis of tetrodotoxin and its analogues in this laboratory. One of the major modifications was to establish a two-step guanidinylation of trichloroacetamid... |
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Activation of glycosyl trichloroacetimidates with perchloric acid on silica (HClO(4)-SiO(2)) provides enhanced alpha-selectivity.
Carbohydr. Res. 345(14) , 2074-8, (2010) Obtaining high stereoselectivity in glycosylation reactions is often challenging in the absence of neighboring group participation. In this study, we demonstrate that activation of glycosyl trichloroacetimidate donors with immobilized perchloric acid on silic... |
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Synthetic studies toward the anthrax tetrasaccharide: alternative synthesis of this antigen
Carbohydr. Res. 356 , 115-31, (2012) The synthesis of the anthrax tetrasaccharide, amenable for conjugation, has been envisaged by both [2+2] and [1+3] approaches from D-fucose and L-rhamnose. The successful route reported herein relies on a [1+3] strategy in which the 1,2-trans-glycosidic linka... |
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Stereoselective rearrangement of trichloroacetimidates: application to the synthesis of alpha-glycosyl ureas.
Org. Lett. 11(11) , 2433-6, (2009) A new method for the stereoselective synthesis of alpha-glycosyl ureas, via nickel-catalyzed [1,3]-rearrangement of glycosyl trichloroacetimidates, has been developed. The alpha-stereoselectivity at the anomeric carbon of the resulting trichloroacetamides dep... |
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Rhodium-catalyzed regio- and enantioselective amination of racemic secondary allylic trichloroacetimidates with N-methyl anilines.
Chem. Commun. (Camb.) 48(94) , 11531-3, (2012) We report the chiral diene ligated rhodium-catalyzed dynamic kinetic asymmetric transformation (DYKAT) of racemic secondary allylic trichloroacetimidates with a variety of N-methyl anilines, providing allylic N-methyl arylamines in high yields, regioselectivi... |
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Influence of the solvent in low temperature glycosylations with O-(2,3,5,6-tetra-O-benzyl-β-D-galactofuranosyl) trichloroacetimidate for 1,2-cis α-D-galactofuranosylation.
Carbohydr. Res. 346(12) , 1495-502, (2011) Glycosylation studies for the construction of 1,2-cis α-linkages with O-(2,3,5,6-tetra-O-benzyl-β-D-galactofuranosyl) trichloroacetimidate (1) and several acceptors, including D-mannosyl and l-rhamnosyl derivatives were performed. The reactions were conducted... |
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Translocation versus cyclisation in radicals derived from N-3-alkenyl trichloroacetamides.
Org. Biomol. Chem. 9(9) , 3180-7, (2011) Under radical reaction conditions, two different and competitive reaction pathways were observed for N-(α-methylbenzyl)trichloroacetamides with a N-3-cyclohexenyl substituent: 1,4-hydrogen translocation and radical addition to a double bond. However, for radi... |
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Rate-dependent inverse-addition beta-selective mannosylation and contiguous sequential glycosylation involving beta-mannosidic bond formation.
Chem. Asian J. 5(5) , 1152-62, (2010) The beta-selectivity of mannosylation has been found to be dependent on the addition rate of the mannosyl trichloroacetimidate donor in an inverse-addition (I-A) procedure. This rate dependent I-A procedure can improve the selectivity of direct beta-mannosyla... |
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Concise synthesis of two natural triterpenoid saponins, oleanolic acid derivatives isolated from the roots of Pulsatilla chinensis.
Carbohydr. Res. 344(11) , 1276-81, (2009) The first synthesis of two natural triterpenoid saponins, which were isolated from the roots of Pulsatilla chinensis and exhibited excellent in vitro cytotoxic activity against HL-60 cells, was concisely achieved in a convergent approach. We employed an odour... |
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Palladacyclic imidazoline-naphthalene complexes: synthesis and catalytic performance in Pd(II)-catalyzed enantioselective reactions of allylic trichloroacetimidates.
J. Org. Chem. 77(4) , 1939-51, (2012) A new family of air- and moisture-stable enantiopure C,N-palladacycles (PIN-acac complexes) were prepared in good overall yield in three steps from 2-iodo-1-naphthoic acid and enantiopure β-amino alcohols. Three of these PIN complexes were characterized by si... |