Nucleic acid related compounds. 25. Syntheses of arabino, xylo, and lyxo-anhydro sugar nucleosides from tubercidin ribo-epoxide

Abstract

. Can J. Chem. 55, 1260Chem. 55, (1977. Treatment of the trans iodohydrin acetate, 4-arnino-7-(3-iodo-3-deoxy-2-O-acetyl-5-0-[2,5,5-trimethyl-1,3-dioxolan-4-on-2-yl]-~-~-xylofuranosyl)pyrrolo[2,3-d]pyrimidine (2) with methanolic ammonia gave 2',3'-anhydrotubercidin (3) in 96% yield. N4,N4,05'-Tribenzoylation of 3 gave 4, which is stabilized against intramolecular cyclization. Treatment of 4 with boron trifluoride etherate (3',5'-benzoxonium ion formation) followed by deblocking gave 4-amino-7-B-D-xylofuranosylpyrrolo[2,3-dlpyrimidine (5) in 91% overall yield from tubercidin (1). The 3',5'-0-isopropylidene derivative (6a) of 5 was mesylated to give 6b which was deprotected in acid and the resulting trans hydroxy mesylate was treated with base to give 4-amino-7-(2,3-anhydro-P-D-lyxofuranosyl)pyrrolo[2,3-d]rmdne (7

Xylotubercidin against herpes simplex virus type 2 in mice

“…Tubercidin was purchased from The Upjohn Co. (Kalamazoo, Mich.). Toyocamycin, sangivamycin, and xylotubercidin (6,35), and the arabinosyl (22), 2'-deoxyribosyl (37), 3'-deoxyribosyl (36), and 2'-deoxyxylosyl derivatives of tubercidin, toyocamycin, and sangivamycin were obtained from M. J. Robins. The synthesis and in vitro biological properties of the sugar-modified analog of tubercidin, toyocamycin, and sangivamycin, which all are pyrrolo [2,3-d]pyrimidine nucleosides, will be published elsewhere.…”