| CPC C07H 21/00 (2013.01) [C07F 9/098 (2013.01); C07H 1/00 (2013.01)] | 17 Claims |
|
1. A functionalized solid support of formula (I), or a salt thereof,
 wherein:
A is a solid support material;
L1 -silyl-C2-4alkylene-NH—C2-10alkylene-NHC(O)—C2-10alkylene;
L2, at each occurrence, is independently —(CH2CH2O)m—, —(CHCH3CH2O)m—, or —(CH2CHCH3O)m—;
G1 is —P(O)(R1)-L3-R2, hydrogen, or PG1;
R1, at each occurrence, is independently —OR1a or R1a;
R1a, at each occurrence, is independently C1-10alkyl, C2-10alkenyl, C2-10alkynyl, C3-10cycloalkyl, or C5-10cycloalkenyl, wherein R1a is optionally substituted with 1-6 substituents independently selected from the group consisting of cyano, halogen, oxo, OH, —OC1-4alkyl, —OC1-4haloalkyl, or C3-6cycloalkyl, the C3-6cycloalkyl being optionally substituted with halogen or C1-4alkyl;
L3 is —(OCH2CH2)p—, —(OCHCH3CH2)p—, —(OCH2CHCH3)p—, —OC2-10alkylene-, —OC0-4alkylene-C3-10cycloalkylene-C0-4alkylene-, or —OC0-4alkylene-phenylene-C0-4alkylene-, wherein the alkylene in L3 is optionally substituted with 1-6 halogen, and the cycloalkylene and phenylene are optionally substituted with 1-4 substituents independently selected from the group consisting of halogen, C1-4alkyl, C1-4haloalkyl, cyano, —OC1-4alkyl, and —OC1-4haloalkyl;
R2 is —NR2aR2b;
R2a is hydrogen, C1-6alkyl, C1-6haloalkyl, C3-6cycloalkyl, or —C1-3alkylene-C3-6cycloalkyl;
R2b is C(O)-L4-G1a, hydrogen, PG2, C(O)-L4-OH, C(O)-L4-OPG3, C(O)-L5-H, C(O)-L5-PG1, C(O)-L5-P(O)(R1)-G1a, C(O)-L5-P(O)(OH)-G1a, or C(O)-L6-G1a, or
R2a and R2b, together with the nitrogen to which they attach form a protected nitrogen atom;
L4 is L7-C(O) or C(O);
L5 is L7-O;
L6 is L7-Si(C1-4alkyl)2;
L7 is a divalent chemical linker composed of atoms selected from the group consisting of carbon, hydrogen, oxygen, nitrogen, sulfur, phosphorus, silicon, and halogen,
wherein
(a) the atoms of the divalent linker are arranged to form an optionally substituted chain, an optionally substituted ring, or a combination of optionally substituted chain(s) and ring(s); and
(b) the chain(s), ring(s), or combination thereof comprise a 1- to 20-membered contiguous linear arrangement of atoms selected from the group consisting of carbon, oxygen, nitrogen, sulfur, phosphorus, and silicon;
G1a is a nucleotide moiety or a nucleoside moiety;
PG1 is a hydroxy protecting group;
PG2 is an amino protecting group;
PG3 is carboxylic acid protecting group;
m and p are independently an integer from 3 to 10; and
n is an integer from 1 to 20.
|