53331-55-8Relevant academic research and scientific papers
Efficient α-mannosylation of phenols: The role of carbamates as scavengers for activated glycosyl donors
Schüler, Peter,Fischer, Sebastiann.,Marsch, Michael,Oberthür, Markus
supporting information, p. 27 - 39 (2013/03/13)
The boron trifluoride activation of trichloroacetimidate donors was found to be an efficient method for the α-mannosylation of tyrosine-containing acceptors. Most notably, these conditions are compatible with the commonly used carbamate protecting groups, whereas trichloroacetimidate activation with trimethylsilyl triflate or the use of glycosyl sulfoxides led to diminished yields in the presence of carbamates. In these cases, the competing reaction of the activated donors with the carbamate group was identified as a problematic side reaction. Taking advantage of this reactivity, various glycosyl carbamates were generated for the first time under non-acidic glycosylation conditions by reaction of different Boc-protected amino acids and dipeptides with glycosyl sulfoxides under triflic anhydride activation. Georg Thieme Verlag Stuttgart · New York.
Practical stereoselective synthesis of β-branched aα-amino acids through efficient kinetic resolution in the phase-transfer-catalyzed asymmetric alkylations
Ooi, Takashi,Kato, Daisuke,Inamura, Koji,Ohmatsu, Kohsuke,Maruoka, Keiji
, p. 3945 - 3948 (2008/02/11)
Phase-transfer-catalyzed alkylation of glycinate Schiff base with racemic secondary alkyl halides proceeded with excellent levels of syn- and enantioselectivities under the influence of chiral quaternary ammonium bromide 1d and 18-crown-6. The alkylation
Acyclic stereoselective boron alkylation reactions for the asymmetric synthesis of β-substituted α-amino acid derivatives
O'Donnell, Martin J.,Cooper, Jeremy T.,Mader, Mary M.
, p. 2370 - 2371 (2007/10/03)
Optically active syn- or anti-β-substituted-α-amino acid derivatives are prepared in 94 to ≥99% ee and 66-98% ds by reaction of the Schiff base acetate of glycine tert-butyl ester with chiral, nonracemic B-alkyl-9-BBN derivatives in the presence of the Cinchona alkaloid, cinchonidine (CdOH) or cinchonine (CnOH), base, and lithium chloride. Copyright
