Adenine chloromercuri derivative

The reaction of 3,4,6-tri-0-acetyl-2-deoxy-2-phthalimido-D-glucopy-ranosyl chloride with the chloromercuri derivative of Ar ,iV -dimethyl-2-(methylthio)adenine, followed by desulfurization and de-O-acylation gave 9-(2-acetamido-2-deoxy-/3-D-glucosyl)-iV ,i -dimethyladenine (69)This... 

A nucleoside derivative of 4-acetamido-4-deoxy-D-xyIofuranose was synthesized by a series of reactions. Partial benzoylation of methyl )8-L-arabinopyranoside produces " methyl 2,3-di-0-benzoyl-j3-L-arabinopyranoside. p-Toluenesulfonylation at 0-4, followed by displacement with sodium azide, gives methyl 4-azido-2,3-di-0-benzoyl-4-deoxy-a-D-xylopyranoside. Hydrogenation, debenzoylation, N-acetylation, and acetolysis yield 4-acetamido-l,2,3,5-tetra-0-acetyl-4-deoxy-D-xylofuranose (D-enantiomorph of 191), which reacts in the presence of titanium tetrachloride in chloroform with chloromercuri-(6-benzoyladenine), giving, after deacylation, 9-(4-acetamido-4-deoxy-)8-D-xylofuranosyl)adenine. ... 

The chloromercuri procedure has also been utilized to prepare the ribonucleosides of 6-methylthiopurine, 6-methylpurine, a number of adenine derivatives, " 8-azapurines, and imidazo[4,5-d]pyrazines. ... 

The titanium chloride-complex procedure, applied to chloromercuri-6-chloropurine (65b), again resulted in an anomeric mixture (66b and 67b), whereas the iV,iV-phthaloylaminoglyco8yl halide gave only the /3-d anomer (66b). Deblocking with amines resulted in concomitant replacement of the 6-chlorine atom, to give the corresponding adenine derivatives (66c). 

---