Iodine Catalysed Tandem Stereoselective Acetalation-Glycosylation of Reducing Sugars Using Acetals/Ketals: Application in the Synthesis of Orthogonally Protected Nucleosides

摘要

A convenient and efficient one pot method has been developed for molecular iodine catalysed tandem synthesis of acetonide protected O-glycosides from reducing sugars and acetals/ketals. Various free sugars reacted smoothly with both acetals and ketals to form orthogonally protected O-glycosides in good yields at room temperature. The method works well in the presence of various external alcohols. Acetonide protected methyl ribofuranoside thus formed was utilized for the synthesis of C-5 protected ribonucleoside derivative.