Compositions for nucleic acid delivery

1. A compound represented by formula XXXIII:

wherein,

R 1 and R 2 are each independently for each occurrence optionally substituted C 10 -C 30 alkyl, optionally substituted C 10 -C 30 alkoxy, optionally substituted C 10 -C 30 alkenyl, optionally substituted C 10 -C 30 alkenyloxy, optionally substituted C 10 -C 30 alkynyl, optionally substituted C 10 -C 30 alkynyloxy, or optionally substituted C 10 -C 30 acyl;

E is OC(O)N(R′);

R 3 has the formula:

wherein

each of Y 1 , Y 2 , Y 3 , and Y 4 , independently, is alkyl, cycloalkyl, aryl, aralkyl, or alkynyl; or

any two of Y 1 , Y 2 , and Y 3 are taken together with the N atom to which they are attached to form a 3- to 8-member heterocycle; or

Y 1 , Y 2 , and Y 3 are all taken together with the N atom to which they are attached to form a bicyclic 5- to 12-member heterocycle;

each R n , independently, is H, halo, cyano, hydroxy, amino, alkyl, alkoxy, cycloalkyl, aryl, heteroaryl, or heterocyclyl;

L 3 is a bond, —N(Q)-, —O—, —S—, —(CR 5 R 6 ) a —, —C(O)—, or a combination of any two of these;

L 4 is a bond, —N(Q)-, —O—, —S—, —(CR 5 R 6 ) a —, —C(O)—, or a combination of any two of these;

L 5 is a bond, —N(Q)-, —O—, —(CR 5 R 6 ) a —, —C(O)—, or a combination of any two of these;

each occurrence of R 5 and R 6 is, independently, H, halo, cyano, hydroxy, amino, alkyl, alkoxy, cycloalkyl, aryl, heteroaryl, or heterocyclyl: or two R 5 groups on adjacent carbon atoms are taken together to form a double bond between their respective carbon atoms: or two R 5 groups on adjacent carbon atoms and two R 6 groups on the same adjacent carbon atoms are taken together to form a triple bond between their respective carbon atoms;

each a, independently, is 0, 1, 2, or 3;

R′ is H, alkyl, heteroalkyl, aralkyl, cyclic alkyl, or heterocyclyl;

wherein

an R 5 or R 6 substituent from any of L 3 , L 4 , or L 5 is optionally taken with an R 5 or R 6 substituent from any of L 3 , L 4 , or L 5 to form a 3- to 8-member cycloalkyl, heterocyclyl, aryl, or heteroaryl group; and

any one of Y 1 , Y 2 , or Y 3 , is optionally taken together with an R 5 or R 6 group from any of L 3 , L 4 , and L 5 , and atoms to which they are attached, to form a 3- to 8-member heterocyclyl group; and

each Q, independently, is H, alkyl, acyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl or heterocyclyl.

2. The compound:

3. The compound of claim 1 , wherein R 3 has the formula:

4. The compound of claim 1 , wherein R 3 has the formula:

5. The compound of claim 1 , wherein R 3 has the formula: