147000-77-9Relevant academic research and scientific papers
Synthesis of pseudonucleosides containing chiral sulfahydantoins as aglycone (II)
Dewynter, Georges,Aouf, Nourreddine,Regainia, Zine,Montero, Jean-Louis
, p. 993 - 1004 (2007/10/03)
A series of chiral sulfahydantoins have been synthesized by alkaline cyclization starting from N-sulfamylaminoacid methyl esters. Regioselective glycosylation of these pseudopyrimidic heterocycles was carried out with a benzyl protecting group on the N-su
The synthesis of chiral sulfahydantoins. Stereochemical aspects and regiospecific protection
Dewynter,Aouf,Criton,Montero
, p. 65 - 76 (2007/10/02)
The enantiospecific synthesis of N2-benzyl-1-thia-2,5-diazolidin-3-one dioxides (sulfa-analogues of hydantoins) was carried out through two convergent pathways starting from chlorosulfonyl isocyanate (CSI) and chiral α-amino- and hydroxyesters. The intermediate carboxylsulfamides (containing 'activated sulfamoyl group') react easily in the Mitsunobu conditions to give ultimately the N-protected sulfa-hydantoins, or symmetric and dissymmetric sulfones of bis-N-aminoesters. The non-racemization during the cyclization of N-sulfamylaminoesters in alkaline conditions was established by chemical and spectroscopic methods (nmr with chiral Eu(hfc)3.
