2-fluorinated riboses and arabinoses and methods of use and synthesis

A compound of formula (I):

• wherein (a) R1 is hydrogen and R2 is selected from the group consisting of
• or (b) wherein R1 is selected from the group consisting of
• and R2 is hydrogen,
• X, Y, and Z are O,
• R3 and R4 are independently selected from the group consisting of hydrogen, F, Cl, Br, and I, with the proviso that R3 and R4 are not both hydrogen,
• n is 1 or 2,
• R8 is selected from the group consisting of hydrogen, COR19, B(OR2)2, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aryl, optionally substituted arylalkyl, F, Cl, Br, I, CF3, optionally substituted alkoxy, NO2, optionally substituted alkylthio, optionally substituted amino, optionally substituted acylthio, hydroxy, mercapto, and optionally substituted thioamido,
• R19 is selected from the group consisting of hydrogen, amino, alkylamino, dialkylamino, hydroxy, alkoxy, and aryloxy,
• R20 is hydrogen or C1-C6 alkyl,
• each of R5, R6, R7, R9, R13, R14, R15, and R17 is independently selected from the group consisting of hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aryl, optionally substituted arylalkyl, F, Cl, Br, I, CF3, optionally substituted alkoxy, optionally substituted aryl, NO2, optionally substituted alkylthio, optionally substituted amino, optionally substituted acylamino, optionally substituted arylamino, optionally substituted acylthio, optionally substituted acyl, optionally substituted acyloxy, hydroxy, mercapto, and optionally substituted thioamido, or any of R5 and R6 taken together, R6 and R7 taken together, R13 and R14 taken together, or R14 and R15 taken together, form a 5- or 6-membered saturated or unsaturated ring,
• R10 and R18 are independently selected from the group consisting of hydrogen, optionally substituted acyl, optionally substituted acyloxy, trialkylsilyl, optionally substituted alkyl, optionally substituted alkylaryl, phosphate, diphosphate, and triphosphate,
• R11 and R12 are independently selected from the group consisting of hydrogen, F, Cl, Br, and I,
• R23 is selected from the group consisting of hydrogen, alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, aryl, heteroaryl, cycloalkyl, and heterocycloalkyl, and
• X− is an anion,
• or a pharmaceutically acceptable salt thereof.

A polymer comprising as a monomeric unit a compound of formula (I):

• wherein R1 is selected from the group consisting of hydrogen, optionally substituted acyl, optionally substituted acyloxy, trialkylsilyl, optionally substituted alkyl, optionally substituted alkylaryl, phosphate, diphosphate, triphosphate,
• R2 is selected from the group consisting of hydrogen, optionally substituted acyl, optionally substituted acyloxy, trialkylsilyl, optionally substituted alkyl, and optionally substituted alkylaryl, phosphate, diphosphate, triphosphate,
• X, Y, and Z are O,
• R3 and R4 are both F or Cl,
• n is 1 or 2,
• R8 is selected from the group consisting of hydrogen, COR19, B(OR2)2, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aryl, optionally substituted arylalkyl, F, Cl, Br, I, CF3, optionally substituted alkoxy, NO2, optionally substituted alkylthio, optionally substituted amino, optionally substituted acylthio, hydroxy, mercapto, and optionally substituted thioamido,
• R19 is selected from the group consisting of hydrogen, amino, alkylamino, dialkylamino, hydroxy, alkoxy, and aryloxy,
• R20 is hydrogen or C1-C6 alkyl,
• each of R5, R6, R7, R9, R13, R14, R15, and R17 is independently selected from the group consisting of hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aryl, optionally substituted arylalkyl, F, Cl, Br, I, CF3, optionally substituted alkoxy, optionally substituted aryl, NO2, optionally substituted alkylthio, optionally substituted amino, optionally substituted acylamino, optionally substituted arylamino, optionally substituted acylthio, optionally substituted acyl, optionally substituted acyloxy, hydroxy, mercapto, and optionally substituted thioamido, or any of R5 and R6 taken together, R6 and R7 taken together, R13 and R14 taken together, or R14 and R15 taken together, form a 5- or 6-membered saturated or unsaturated ring,
• R10 and R18 are independently selected from the group consisting of hydrogen, optionally substituted acyl, optionally substituted acyloxy, trialkylsilyl, optionally substituted alkyl, optionally substituted alkylaryl, phosphate, diphosphate, and triphosphate,
• R11 and R12 are independently selected from the group consisting of hydrogen, F, Cl, Br, and I,
• R23 is selected from the group consisting of hydrogen, alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, aryl, heteroaryl, cycloalkyl, and heterocycloalkyl, and
• X− is an anion,
• or a pharmaceutically acceptable salt thereof.