Ribofuranosyl cyanide

Bobek and FarkaS40 reported the preparation of crystalline 2,3,5-tri-0-benzoyl-/3-D-ribofuranosyl cyanide (82) from the corresponding bromide (81). Their work was based on initial experiences of Hel-... 

In the presence of a Lewis acid such as SnCh, BF3 OEt2, ot TiC104, TMS-CN reacts with acetals to give cyanohydrin ethers. o-Ribofuranosyl cyanide, an important intermediate of C-nucleoside synthesis, is prepared from a furanosyl acetate (Scheme 23). ... 

Furanoid (and Pyrrolidine) Compounds. - For making 2,3,5-tri-O-ben-zoyl-p-D-ribofuranosyl cyanide it is reported to be better to use KCN rather than... 

D-ribofuranosyl-cyanide, in turn best made from the 1-acetyl... 

Addition reactions to unsaturated C-glycosides have continued to be utilized to synthesize C-nucleosides. Thus 2,3,5-tri-0-benzoyl-/3-D-ribofuranosyl cyanide with sodium azide-ammonium chloride in DMF gave the tetrazole (72) in 72% yield. Treatment of (72) with acetic anhydride gave the 1,3,4-oxadiazole nucleoside (73). The benzothiazole (74) was obtained from the ribosyl cyanide by reaction with 2-aminothiophenol. Analogous compounds were derived from jS-D-ribo-, 8-D-xylo-, and j3-D-galactopyranosyl cyanides. A similar reaction has been used by a different group to synthesize a-D-arabinosyl tetrazole (75). Reaction of 3,4-di-0-benzoyl-2,5-anhydro-D-... 

A one flask synthesis of 2,3,5-tri-O-benzoyl-P-D-ribofuranosyl cyanide from the corresponding p-ribosyl acetate (with Me3SiCN, SnCl4, MeCN) has been detailed. ... 

Other syntheses have utilized C-glycoside precursors. Reaction of 2,3,5-tri-0-benzoyl-6-D-ribofuranosyl cyanide with hydrogen selenide gave the corresponding seleno-amide which could by cycl-... 

A further one-pot synthesis gives tri-0-benzoyl-p-J>-ribofuranosyl cyanide in 86% yield, and a 2-deoxy analogue was made using (Tanodiethylaluminium. ... 

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