Lithium Hydroxide → HCID 178418270, compound
Reaction equation
[C@@H:1]1([N:10]2[C:20]3[N:19]=[C:17]([NH2:18])[NH:16][C:14](=[O:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].C(CC[O:25][P:26](=O)([OH:28])[OH:27])#N.C1(N=C=NC2CCCCC2)CCCCC1.[OH-].[Li+]>CC(C)=O.N1C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[CH:11]1[N:10]([C@@H:1]2[O:9][C@H:6]([CH2:7][O:8][P:26]([OH:28])([OH:27])=[O:25])[C@@H:4]([OH:5])[C@H:2]2[OH:3])[C:20]2[NH:19][C:17]([NH2:18])=[N:16][C:14](=[O:15])[C:13]=2[N:12]=1Participants
Procedure
For example, the aforesaid guanosine is reacted with zinc chloride in acetone to introduce an isopropylidene group into the 2'- and 3'-hydroxyl groups of guanosine and reacting the product with 2-cyanoethylphosphoric acid in pyridine in the presence of dicyclohexyl carbodiimide (DCC) to cyanophosphorylate the 5'-position. The resulting compound is subjected to a deprotection reaction with lithium hydroxide and then a cation exchange resin (H+) to obtain 5'-GMP. This reaction can be carried out, for example, in the following manner. One mole of 2',3'-O-isopropylideneguanosine and 4 moles of 2-cyanoethylphosphoric acid are dissolved in 50% aqueous pyridine solution. The solvent is evaporated at 30° C. under reduced pressure. The residue is dissolved in pyridine and dicyclohexyl carbodiimide (DCC) is added, and the mixture is allowed to stand for 18 hours at room temperature. A small amount of water is added. The mixture is left to stand for 1 hour, and then concentrated under reduced pressure. A 0.4N aqueous solution of lithium hydroxide is added and the mixture is boiled under reflux for 1 hour.
Sources & evidence
- ORD record
- ord-7df4e8553728499da3fe31fcbcb17893
- Source dataset
- uspto-grants-1986_11
- Patent number
- US04621076
Reaction notes
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