Modified Synthesis of 3′-OTBDPS-Protected Furanoid Glycal
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Citation of Original Publication
Temburnikar, Kartik, Zhibo Zhang, and Katherine Seley-Radtke. “Modified Synthesis of 3′-OTBDPS-Protected Furanoid Glycal.” Nucleosides, Nucleotides & Nucleic Acids 31, no. 4 (April 1, 2012): 319–27. https://doi.org/10.1080/15257770.2012.656212.
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This is an Accepted Manuscript of an article published by Taylor & Francis in Nucleosides, Nucleotides & Nucleic Acids on 2012-03-23, available online: https://www.tandfonline.com/doi/full/10.1080/15257770.2012.656212.
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.