Regioselective glycosylation: synthesis of alpha-indoline nucleosides.
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.
Brown
Kenneth L
KL
Department of Chemistry and Biochemistry, Ohio University, Athens, Ohio 45701, USA. brownk3@ohiou.edu
Chandra
Tilak
T
Zou
Shawn
S
Valente
Edward J
EJ
D018360:Crystallography, X-Ray; D006031:Glycosylation; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012263:Ribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry
D007211:Indoles; D012263:Ribonucleosides