title: Modified synthesis of 3'-O-TBDPS-protected furanoid glycal.
abstract: Thermolytic cleavage of 3'-OH protected thymidine is the most common method of preparing furanoid glycals. We have observed that glycosidic bond cleavage is more facile when the 5'-OH of thymidine was also protected with a silyl group. Addition of trimethylsilyl chloride facilitated cleavage of the glycosidic bond; thus, both modifications are required for the formation of the furanoid glycal. Investigations into the selective deprotection of 5'-silyl versus 3'-silyl and subsequent glycosidic bond cleavage are reported herein.
authors.affiliation: Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, Maryland 21250, USA.
authors.forename: Kartik
authors.initials: K
authors.lastname: Temburnikar
authors.forename: Zhibo
authors.initials: Z
authors.lastname: Zhang
authors.forename: Katherine
authors.initials: K
authors.lastname: Seley-Radtke
mesh_terms: D012833:Siloxanes / Q000737:chemistry; D013936:Thymidine / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D012833:Siloxanes; D013936:Thymidine