Reactions of per-O-benzoyl-β-D-Galf isothiocyanate, a chiral resolving agent
1997; Elsevier BV; Volume: 53; Issue: 47 Linguagem: Inglês
10.1016/s0040-4020(97)10070-9
ISSN1464-5416
AutoresCarla Marino, Oscar Varela, Rosa M. de Lederkremer,
Tópico(s)Amino Acid Enzymes and Metabolism
ResumoTetra-O-benzoyl-β-D-galactofuranosyl isothiocyanate (1) was readily prepared (90% yield) from per-O-benzoyl-D-galactofuranose, via the glycosyl bromide. Reaction of 1 with alcohols, amines and amino acids afforded a variety of glycosylthiourethanes and glycosylthioureides. The isothiocyanate 1 showed to be useful as a chiral resolving agent. The resolution of racemic primary and secondary amines and aminoalcohols was readily accomplished, in analytical and preparative scale, by condensation of such compounds with 1.
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