H. Hrebabecky et A. Holy, SYNTHESIS OF DEOXY, DIDEOXY AND DIDEHYDRODIDEOXY ANALOGS OF -(4-C-HYDROXYMETHYL-ALPHA-L-PENTOFURANOSYL)ADENINE, Collection of Czechoslovak Chemical Communications, 59(7), 1994, pp. 1654-1664
Condensation of i-O-benzoyl-4-C-benzoyloxymethyl-L-arabinofuranose wit
h N6-benzoyladenine, catalyzed with tin tetrachloride, afforded nucleo
side I, which upon partial deacetylation and subsequent mesylation was
converted into O-methanesulfonyl-alpha-L-arabinofuranosyl)adenine (II
I). 9-(2,5,6-Tri-O-acetyl-4-C-acetoxy methyl-3-0-methane lfonyl-alpha-
L-arabinofuranosyl)-N6-benzoyladenine (V) was obtained by condensation
of 1,2,5-tri-0 -4-C-acetoxymethyl-3-0-methanesulfonyI-L-arabinose wit
h N6-benzoyladenine. Reaction of mesyl derivatives III and V with meth
anolic sodium methoxide afforded 2',3'-anhydro nucleosides VIa and VII
a, which were acetylated to give xymethyl-2,3-anhydro-alpha-L-ribofura
nosyl)adenine (VIb) and xymethyl-2,3-anhydro-alpha-L-lyxofuranosyl)ade
nine (VIIb). Epoxy derivative VIb was cleaved with bromotrimethylsilan
e to l-2-bromo-2-deoxy-alpha-L-arabinofuranosyl)adenine (VIIIa); the s
ame reaction with epoxy derivative VIIb afforded a mixture of 9-(5-0-a
cetyl-4-C-acetoxy hyl-2-bromo-2-deoxy-alpha-L-xylo-furanosyl)adenine (
IXa) and l-3-bromo-3-deoxy-alpha-L-arabinofuranosyl)adenine (Xa). Thei
r dehalogenation with tributylstannane and subsequent deacetylation le
d to droXyMethyl-alpha-L-erythro-pentofuranosyl)adenine (VIIIc), ydrox
y-methyl-alpha-L-threo-pentofuranosyl)adenine (IXc) and hydroxymethyl-
alpha-L-threo-pentofuranosyl)adenine (Xc). l-2-bromo-2-deoxy-alpha-L-a
rabinofuranosyl)adenine (VIIId), prepared by acetylation of VIIIa, on
reductive elimination with Cu/Zn couple and subsequent deacetylation a
fforded methyl-alpha-L-glycero-pent-2-enofuranosyl)adenine (XIb). roxy
methyl-alpha-L-glycero-pentofuranosyl)-adenine (XIIb) was obtained eit
her by catalytic hydrogenation of bromo derivative VIIId, followed by
deacetylation, or by catalytic hydrogenation of didehydro derivative X
Ib. The nucleosides synthesized were tested for antiviral activity.