Carbohydrate conjugates as delivery agents for oligonucleotides

An iRNA agent comprising a compound having the structure shown in formula (I′):

• wherein:
• A and B are each independently for each occurrence O, N(RN) or S;
• X and Y are each independently for each occurrence H, a protecting group, a phosphate group, a phosphodiester group, an activated phosphate group, an activated phosphite group, a phosphoramidite, a solid support, —P(Z′)(Z″)O-nucleoside, —P(Z′)(Z″)O-oligonucleotide, a lipid, a PEG, a steroid, a polymer, a nucleotide, annucleoside, —P(Z′)(Z″)O—R1-Q′—R2—OP(Z′″)(Z″″)O-oligonucleotide, or an oligonucleotide, —P(Z′)(Z″)-formula (I), —P(Z′)(Z″)- or -Q-R;
• R is L1or has the structure shown in formula (II)-(V)
• q2A, q2B, q3A, q3B, q4A, q4B, q5A, q5B and q5C represent independently for each occurrence 0-20 and wherein the repeating unit can be the same or different;
• Q and Q′ are independently for each occurrence absent, —(P7-Q7-R7)p-T7- or -T7-Q7-T7′-B-T8′-Q8-T8;
• P2A, P2B, P3A, P3B, P4A, P4B, P5A, P5B, P5C, P7, T2A, T2B, T3A, T3B, T4A, T4B, T4A, T5B, T5C, T7, T7′, T8 and T8′ are each independently for each occurrence absent, CO, NH, O, S, OC(O), NHC(O), CH2, CH2NH or CH2O;
• B is —CH2—N(BL)—CH2—;
• BL is -TB-QB-TB′-Rx;
• Q2A, Q2B, Q3A, Q3B, Q4A, Q4B, Q5A, Q5B, Q5C, Q7, Q8 and QB are independently for each occurrence absent, alkylene, substituted alkylene wherein one or more methylenes can be interrupted or terminated by one or more of O, S, S(O), SO2, N(RN), C(R′)═C(R″), C≡C or C(O);
• TB and TB′ are each independently for each occurrence absent, CO, NH, O, S, OC(O), OC(O)O, NHC(O), NHC(O)NH, NHC(O)O, CH2, CH2NH or CH2O;
• Rx is a lipophile, or a cationic lipid;
• R1, R2, R2A, R2B, R3A, R3B, R4A, R4B, R5A, R5B, R5C, R7 are each independently for each occurrence absent, NH, O, S, CH2, C(O)O, C(O)NH, NHCH(Ra)C(O), —C(O)—CH(Ra)—NH—, CO, CH═N—O,
• or heterocyclyl;
• L1, L2A, L2B, L3A, L3B, L4A, L4B, L5A, L5B and L5C are each independently for each occurrence a carbohydrate;
• R′ and R″ are each independently H, C1-C6 alkyl, OH, SH or N(RN)2;
• RN is independently for each occurrence methyl, ethyl, propyl, isopropyl, butyl or benzyl;
• Ra is H or amino acid side chain;
• Z′, Z″, Z″′ and Z″″ are each independently for each occurrence O or S;
• p represent independently for each occurrence 0-20.