Oligomeric phosphite, phosphodiester, Phosphorothioate and phosphorodithioate compounds and intermediates for preparing same

A compound having the Formula:

• ##STR20## wherein:
• each R.sub.1, is, independently, H, --OH, --F, or --O--X.sub.3 --D;
• D is H, amino, protected amino, alkyl substituted amino, imidazole, or (--O--X.sub.3).sub.p, where p is 1 to about 10;
• R.sub.2 is a hydroxyl protecting group, or a linker connected to a solid support;
• R.sub.3 is hydrogen, a hydroxyl protecting group, or a linker connected to a solid support, provided that R.sub.2 and R.sub.3 are not both simultaneously a linker connected to a solid support;
• X.sub.1 is O or S;
• each X.sub.2 is O or S;
• each X.sub.3 is alkyl having from 1 to 10 carbons;
• each Q is --X.sub.1 H or --X.sub.1 --CH.sub.2 --CH.dbd.CH--CH.sub.2 --Z;
• m and n are each independently an integer from 0 to about 50, provided that the sum of m and n does not exceed 50;
• each B, independently, is a naturally occurring or non-naturally occurring nucleobase or a protected naturally occurring or non-naturally occurring nucleobase;
• and
• Z is CN, halogen, NO.sub.2, alkaryl, sulfoxyl, sulfonyl, thio, substituted sulfoxyl, substituted sulfonyl, or substituted thio, wherein the substituents are selected from the group consisting of alkyl, aryl, or alkaryl.

An oligomeric compound comprising a moiety having the Formula IX;

• ##STR21## wherein:
• Z is CN, halogen, NO.sub.2, alkaryl, sulfoxyl, sulfonyl, thio, substituted sulfoxyl, substituted sulfonyl, or substituted thio, wherein the substituents are selected from the group consisting of alkyl, aryl, or alkaryl;
• and
• X.sub.1 is O or S;
• prepared by the steps of:
• (a) providing a compound having the Formula II:
• ##STR22## wherein each R.sub.1, is, independently, H, --OH, --F, or --O--X.sub.3 --D;
• X.sub.3 is alkyl having from 1 to 10 carbons;
• D is H, amino, protected amino, alkyl substituted amino, imidazole, or (--O--X.sub.3).sub.p, where p is 1 to about 10;
• each X.sub.2 is O or S;
• R.sub.3 is hydrogen, a hydroxyl protecting group, or a linker connected to a solid support:
• each B, independently, is a naturally occurring or non-naturally occurring nucleobase or a protected naturally occurring or non-naturally occurring nucleobase;
• n is 0 to about 50;
• each Q is --X.sub.1 H or --X.sub.1 --CH.sub.2 --CH.dbd.CH--CH.sub.2 --Z;
• R.sub.5 is --N(R.sub.6).sub.3, or a heterocycloalkyl or heterocycloalkenyl ring containing from 4 to 7 atoms, and having up to 3 heteroatoms selected from the group consisting of nitrogen, sulfur, and oxygen;
• R.sub.6 is straight or branched chain alkyl having from 1 to 10 carbons;
• (b) reacting the compound of Formula II with a compound having the Formula III:
• ##STR23## wherein R.sub.3a is hydrogen;
• and R.sub.2 is a hydroxyl protecting group, or a linker connected to a solid support;
• (c) oxidizing the product of step (b) to form a further compound having the Formula III, wherein R.sub.3a is hydrogen, a hydroxyl protecting group, or a linker connected to a solid support.