CPC C07H 21/04 (2013.01) [C07F 9/093 (2013.01); C07F 9/098 (2013.01); C07F 9/65515 (2013.01); C07H 21/00 (2013.01); C07H 21/02 (2013.01); C12N 15/1068 (2013.01); C12N 15/113 (2013.01); C40B 50/18 (2013.01)] | 33 Claims |
1. A solid support according to Formula I
![]() wherein:
CPG is controlled pore glass;
m is 2, 3, 4, 5 or 6;
x is 1, 2, 3, 4 or 5;
y is from 2 to 12;
n is 3, 4, 5, 6, 7, 8, 9 or 10;
R2 is H,
![]() p is 2, 3, 4, 5, 6, 7, 8, 9 or 10;
R3 is H or
![]() R4 is H or OR6;
R is PG or a nucleic acid sequence;
R6 is pixyl, TBDMS, TBDPS, TMS, TES, or TIPS;
T is 1, 2, 3, or 4;
BP is a nucleic acid base where an exocyclic amine, if present, is protected;
PG is a protecting group; and
each R1 independently is a thermolabile phosphate protecting group having a structure
![]() wherein:
X is O or S;
R7 is H, Ra, ORa, SRa, or N(Rb)2;
Ra is Rd;
Rb is H, Rd or two Rbs together with the nitrogen to which they are attached, form a 3- to 7-membered heterocyclyl;
Z is O, S, N(Rc), C(Rc)2 or C(Rc)2C(Rc)2;
each Rc independently is H or Rd, or one Rd in combination with the C═X moiety and one Ra or Rb from R7 together form a 3- to 7-membered cycloaliphatic or heterocyclyl ring;
Rd is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or aralkyl;
each R8 independently is H or Rd, or one R8 together with Z forms an aryl ring;
each R9 independently is H or Rd, or one R9 and one R8 together with the atoms to which they are attached, forms a moiety having a formula
![]() wherein r is 0 to 6; and
each R10 independently is H, C1-6alkyl, NO2, —N(C1-6alkyl)2, —OC1-6alkyl, —SC1-6alkyl, —CN, or halogen, provided that the aromatic ring substituted with R10 is one carbon removed from the phosphate oxygen of Formula I.
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