Novel indoline ribonucleosides with the alpha-N-glycoside configuration are synthesized with very high regioselectivity in 90-96%yield, using TMS protected indolines and 2,3-O-(1-methylethylidene)-5-O-(triphenylmethyl)-alpha/beta-D-ribofuranose. The structures of these ribonucleosides were elucidated with X-ray crystallography as well as 2D (NOESY, COSY, and HMQC) NMR spectroscopy.
Nucleic acids U 0700Regioselective Glycosylation: Synthesis of α-Indoline Nucleosides. -The synthesis of novel α-indoline nucleosides (V) with very high regioselectivity and in high yields is described. An X-ray diffraction structure of (Va) is also presented. -(BROWN*, K. L.; CHANDRA, T.; ZOU, S.; VALENTE, E. J.; Nucleosides, Nucleotides Nucleic Acids 24 (2005) 8, 1147-1165; Dep. Chem. Biochem., Ohio Univ., Athens, OH 45701, USA; Eng.) -D. Singer 08-182
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