Triterpene saponin variants, methods of synthesis and use thereof

A compound of formula (I) or a pharmaceutically acceptable salt thereof,

• wherein G is hydrogen, a branched trisaccharide of formula V or a stereoisomer of formula V
• wherein W is CHO
• wherein each occurrence of RP is independently hydrogen or ORx;
• wherein each occurrence of Rx is independently hydrogen or an optionally substituted group selected from 6-10-membered aryl, benzyl, C1-6 aliphatic, or C1-6 heteroaliphatic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;
• or two Rx are taken together to form a 5-7-membered heterocyclic ring having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;
• wherein each occurrence of Rx′ is independently an optionally substituted group selected from 6-10-membered aryl, benzyl, C1-6 aliphatic, or C1-6 heteroaliphatic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;
• or two Rx′ are taken together to form a 5-7-membered heterocyclic ring having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;
• wherein each occurrence of Ry is OH or ORx;
• wherein is a single or double bond;
• wherein V is hydrogen or ORx;
• wherein the —X—Z moiety is selected from the group consisting of
• wherein Z comprises a carbohydrate domain having the structure:
• wherein each occurrence of R1 is Rx or a carbohydrate domain having the structure:
• wherein each occurrence of a, b, and c is independently 0, 1, or 2;
• wherein d is an integer from 1-5, wherein each d bracketed structure may be the same or different;
• with the proviso that the d bracketed structure represents a furanose or pyranose moiety, and the sum of b and c is 1 or 2;
• wherein R0 is hydrogen or an optionally substituted moiety selected from the group consisting of acyl, C1-10 aliphatic, C1-6 heteroaliphatic, 6-10-membered aryl, arylalkyl, 5-10-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur, 4-7-membered heterocyclyl having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;
• wherein each occurrence of Ra, Rb, Rc, and Rd is independently hydrogen, halogen, OH, OR, ORx, NR2, NHCOR, or an optionally substituted group selected from acyl, C1-10 aliphatic, C1-6 heteroaliphatic, 6-10-membered aryl, arylalkyl, 5-10-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur;
• 4-7-membered heterocyclyl having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur, wherein each occurrence of R is independently hydrogen, an optionally substituted group selected from acyl, arylalkyl, 6-10-membered aryl, C1-12 aliphatic, or C1-12 heteroaliphatic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;
• or two R on the same nitrogen atom are taken with the nitrogen to form a 4-7-membered heterocyclic ring having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;
• wherein R2 is NHC(O)R4, OC(O)R4, OC(O)OR4, OC(O)NHR4, OC(O)SR4, NHC(O)OR4, NHC(O)NHR4, NHC(O)N(R4)2, NHR4 or N(R4)2;
• wherein R3 is hydrogen, halogen, CH2OR1, or an optionally substituted group selected from the group consisting of acyl, C1-10 aliphatic, C1-6 heteroaliphatic, 6-10-membered aryl, arylalkyl, 5-10-membered heteroaryl having 1-4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur, and 4-7-membered heterocyclyl having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;
• wherein R4 is T-Rz, wherein T is a covalent bond or a bivalent C1-12 saturated or unsaturated, straight or branched, aliphatic or heteroaliphatic chain, and
• wherein Rz is hydrogen, halogen, C(O)ORq, NC(O)ORq, ORq, NHC(O)Rq, ORq, SRq, NHC(S)Rq, OC(O)Rq, OC(O)ORq, OC(O)NHRq, OC(O)SRq, NHC(O)ORq, NHC(O)NHRq, NHC(O)N(Rq)2, NHRq or N(Rq)2, or an optionally substituted group selected from acyl, arylalkyl, heteroarylalkyl, C1-6 aliphatic, 6-10-membered aryl, 5-10-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur, 4-7-membered heterocyclyl having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur;
• or two Rq on the same nitrogen atom are taken with the nitrogen to form a 4-7-membered heterocyclic ring having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur, and
• wherein Rq is hydrogen, a detectable label, a protecting group, an optionally substituted group selected from acyl, arylalkyl, 6-10-membered aryl, C1-12 aliphatic, and C1-12 heteroaliphatic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur, or
• an optionally substituted group selected from acyl, arylalkyl, 6-10-membered aryl, C1-12 aliphatic, and C1-12 heteroaliphatic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur, wherein the optionally substituted group further comprises a detectable label.