Adenosine Monophosphate → 6-Chloropurine riboside-5'-O-monophosphate sodium salt
Reaction equation
[P:1]([O:5][CH2:6][C@H:7]1[O:11][C@@H:10]([N:12]2[C:21]3[N:20]=[CH:19][N:18]=[C:16](N)[C:15]=3[N:14]=[CH:13]2)[C@H:9]([OH:22])[C@@H:8]1[OH:23])([OH:4])([OH:3])=[O:2].C1N=C([Cl:30])C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C=2N=1.O=P(Cl)(Cl)Cl>O>[CH:19]1[N:18]=[C:16]([Cl:30])[C:15]2[N:14]=[CH:13][N:12]([C@@H:10]3[O:11][C@H:7]([CH2:6][O:5][P:1]([OH:4])([OH:3])=[O:2])[C@@H:8]([OH:23])[C@H:9]3[OH:22])[C:21]=2[N:20]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
N6-(ω-amino-linker) adenosine 5′-monophosphate can be prepared by contacting 6-chloropurine riboside first with POCl3 then water to produce 6-chloropurine riboside 5′-monophosphate. This intermediate can be reacted with a diamine to produce an N6-(ω-amino-linker) adenosine 5′-monophosphate. Diamines include ethylenediamine (EDA), 1,4-butanediamine (BDA), 1,6-hexanediamine (HDA), 2,2′-oxydiethylamine (ODEA), 2,2′-(ethylenedioxy)diethylamine (EDODEA), and 4,7,10-trioxa-1,13-tridecanediamine (TOTDDA). These diamines provide linkers of (CH2)2, (CH2)4, (CH2)6, C2H4OC2H4 and C3H6OC2H4OC2H4OC3H6, respectively. Additional diamines (and polyamines) such as spermidine (NH2(CH2)3NH(CH2)4NH2), spermine, (NH2(CH2)3NH(CH2)4NH(CH2)3NH2), polyethylene glycol diamines (H2N-PEG-NH2), 1,4-bis(3-aminopropoxy)butane (H2N(CH2)3O (CH2)4O(CH2)3NH2), bis(3-aminopropyl)amine(H2N(CH2)3NH(CH2)3NH2), tris(2-aminoethyl)amine(N(CH2CH2NH2)3), 1,8-diaminooctane (H2N(CH2)8NH2), 1,10-diaminodecane (H2N(CH2)10NH2), and 1,12-diaminododecane (H2N(CH2)12NH2), can also be used.
Sources & evidence
- ORD record
- ord-43202d5aec2b4a489fd7820c604fe8e6
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07323319B2
Reaction notes
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