An alternative synthesis of anomeric methyl 2-deoxy-4-thio-D-erythro-pentofuranosides

Preparation of 2,3,5-Tri-O-benzyl-4-thio-L-arabino-furanosides and the Corresponding 4′-Thionucleoside Analogues

“…This two-step process gave an 84% yield of the openchain dithioacetal 4. This high yield demonstrates the posand 2-deoxy-4-thio--ribose [4,5] derivatives are the most popular compounds, because they are precursors for un-sibility to use the protected -xylose derivative 3 directly in contrast to the analogous 2,3,5-tri-O-benzyl--lyxo-funatural 4Ј-thionucleosides [6,7] and 2Ј-deoxy-4Ј-thionucleosides. [8,9] In 1995 Barascut and Imbach published the first ranose which requires deprotection in the 1-position.…”

A Short and Efficient Synthesis of l-Thioarabinose Derivative: A Versatile Synthon for the Synthesis of l-2‘-Deoxy- 2‘,2‘-disubstituted-4‘-thionucleosides

“…4‘-Thionucleosides, which are bioisosteric to clinically useful 4‘-oxonucleosides, show interesting activities such as antibiotic, antiviral, and antineoplastic . Despite these encouraging results and other inherent advantages, such as having a more stable glycosyl bond and increased metabolic stability, difficulties in accessing the requisite 4-thiosugars, which normally involves numerous and low-yielding steps, have prevented their development as clinical agents. Although several groups published improved syntheses of d -2‘-deoxy-4‘-thio-, d -4‘-thioribo-, and d -2‘,3‘-dideoxy-4‘-thionucleosides in the early 1990s, the synthesis of 4-thiosugars continues to be a challenge for the synthesis of 4‘-thionucleosides.…”

4′-Thio-5-Ethyl-2′-Deoxyuridine5′-Triphosphate (TEDUTP): Synthesis and Substrate Properties in DNA-Synthesizing Systems

“…The synthesis of the first 4"-thlo-z -deoxynucleoside; 5-f1u-oro-a:-thio-z -deoxyuridine (Fu and Bobeck, 1978) followed a report on a multi-stage synthesis of a suitable sugar moiety (Fu and Bobeck, 1976). Recently (Dyson et al, 1991a), an efficient synthesis of benzyl 3,5-di-Q-benzyl-2-deoxy-1-thio-o-erythro-pentofuranoside which could be used in the synthesis of 4"-thlo-z -deoxynucleoside analogues was described.…”