Methyl 4-Deoxy-4-mercapto-D-ribofuranoside¹

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

“…In the next step sulfur prepare such compounds with a minimum number of steps. In 1964 Whistler et al [1] reported the synthesis of methyl was introduced into the sugar moiety by using phenylmethanethiol in the presence of concentrated hydrochloric 4-deoxy-4-thio--ribo-furanoside Ϫ one of the earliest publications in this research area. Of course 4-thio--ribose [2,3] acid.…”

A Facile and Practical Synthesis of Peracylated 4-Thio-d-ribofuranoses from d-Glucose

“…Over the past 15 years, 4‘-thionucleosides ( 1 ), in which the lactol ring oxygen is replaced by a sulfur atom, have attracted much attention due to their potent biological activity and unique metabolic stability. 1a, Furthermore, certain 4‘-thionucleosides, when incorporated into RNA strands, lead to enhanced thermal stability of the resulting modified RNA duplex . As the parent building block for 4‘-thionucleosides, 4-thiopentofuranoses have been the subject of many synthetic efforts since the pioneering work of Reist and Whistler . A literature survey revealed that it usually required lengthy steps and high-cost starting materials, such as unnatural carbohydrates, and the overall yields were often unsatisfactory.…”

“…Improved syntheses of 4-thiofuranoses of l - arabino , 2-deoxy- d - ribo , and d - galacto configurations have appeared in recent years; however, the practical synthesis of 4-thio- d -ribofuranose ( 2 ) still remains a challenge, and this has presumably impeded the development of 4‘-thioribonucleosides. To our knowledge, there are only a handful of syntheses of 2 and its derivatives, all starting from costly l -lyxose. , As an alternative, Matsuda and Yoshimura recently published elegant new protocols for the synthesis of 4‘-thioribonucleosides via the Pummerer reaction 8b, we felt that an efficient preparation of 2 and its peracyl derivatives would suffice to make 4‘-β-thioribonucleosides more accessible.…”