5'deoxy-5'-substituted adenosines

DETAILED DESCRIPTION OF THE INVENTION To prepare the compounds of this invention, an adenosine derivative with a leaving group at C-5' and with the 2'- and 3'-hydroxyls either blocked or unblocked, depending upon later steps, is treated with the appropriate amine, either the direct side chain precursor, or a simple amine, which after introduction into the nucleoside, is alkylated on nitrogen with a side chain precursor.
At this stage, the side chain either ends with an alcohol or primary amine, or is deblocked (i.
e.
, phthalimide to amino) to be one of these two groups.
The various end groups are then introduced by standard methodology.
If necessary, the 2', 3'-blocking group is then removed to complete the synthesis.
The specific procedures for certain compounds are presented in the examples which follow.
In these examples, MeOH, EtOH, DMF, THF, Me.
sub.
2 CO, and Et.
sub.
2 O stand for, respectively, methyl alcohol, ethyl alcohol, N,N-dimethylformamide, tetrahydrofuran, acetone, and ethyl ether.
All percentages recited in the examples, unless otherwise identified, refer to yield of product.
The underlined numbers in the examples, except for those numbers in the headings which indicate a quantity of complexed solvent (e.
g.
, H.
sub.
2 O and H.
sub.
2 SO.
sub.
4), refer to the compounds indicated by the corresponding numbers in Table 2 which follows.
In Table 2, Ad stands for the group ##STR18##
TABLE 2
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(1) R.
sub.
1 = R.
sub.
2 = H; R.
sub.
3 = Cl
(2)
##STR19##
(3) R.
sub.
1, R.
sub.
2 = H;
##STR20##
(4)
##STR21##
(5)
##STR22##
##STR23##
(6) R.
sub.
1 = R.
sub.
2 = H; R.
sub.
3 = N(CH.
sub.
3)CH.
sub.
2 CH.
sub.
2
CH.
sub.
2 ONH.
sub.
2.
1.
5H.
sub.
2 SO.
sub.
4
(7)
##STR24##
(8)
##STR25##
##STR26##
(9) R.
sub.
1 = R.
sub.
2 = H; R.
sub.
3 = N(CH.
sub.
3)CH.
sub.
2 CH.
sub.
2
ONH.
sub.
2.
1.
5H.
sub.
2 SO.
sub