Trityl chloride → HCID 136332169, compound

HRID 1731285Notes

Reaction equation

HRID 1731285 reaction equation
P([O:5][C@@H:6]1[C@@H:10]([CH2:11][OH:12])[O:9][C@@H:8]([N:13]2[C:23]3[N:22]=[C:20]([NH2:21])[NH:19][C:17](=[O:18])[C:16]=3[N:15]=[CH:14]2)[C@@H:7]1[OH:24])(O)(O)=O.P(O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2N=C(N)NC(=O)C=2N=C1)(O)(O)=O.[C@@H]1(N2C3N=C(N)NC(=O)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1O.[C:69](Cl)([C:82]1[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=1)([C:76]1[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1)[C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1>N1C=CC=CC=1>[C:69]([CH:11]([OH:12])[C@H:10]1[O:9][C@@H:8]([N:13]2[C:23]3[N:22]=[C:20]([NH2:21])[NH:19][C:17](=[O:18])[C:16]=3[N:15]=[CH:14]2)[C@H:7]([OH:24])[C@@H:6]1[OH:5])([C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)([C:82]1[CH:83]=[CH:84][CH:85]=[CH:86][CH:87]=1)[C:76]1[CH:77]=[CH:78][CH:79]=[CH:80][CH:81]=1

Participants

6

Reactant 4

HCID 6456Trityl chlorideHCID 135398635GuanosineHCID 1353987273'-Guanylic acidHCID 135460966Reactive Red 49

Product 1

HCID 136332169HCID 136332169, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Guanosine 3'-monophosphate (3'-GMP), a compound of formula (I) in which Y is H2PO3 and X and Z are hydrogen atoms, and guanosine 2'-monophosphate (2'-GMP), a compound of formula (I) in which X is H2PO3 and Z and Y are hydrogen atoms, can be obtained in the following manner in accordance with the method of Brown and Todd [D. M. Brown and A. R. Todd, J. Chem. Soc., 44 (1952)]. Specifically, guanosine and trityl chloride are reacted in anhydrous pyridine at 60° C. for 3 days to obtain 5'-tritylguanosine as a result of selective tritylation of the 5'-position. The resulting 5'-tritylguanosine is dissolved in pyridine, and while cooling the solution at -20° C., diphenylphosphoryl chloride was added to obtain a mixture of a trityl derivative of 2'-monophosphate of guanosine and 3'-monophosphate of guanosine. The mixture is dissolved in 80% acetic acid, and the solution is heated under reflux to remove the trityl group to obtain a mixture of 2'-GMP and 3'-GMP. The mixture is charged onto a column of Dowex 1® (formic acid type). The column is eluted with 0.1N formic acid to obtain guanosine 2'-monophosphate as an eluate, and with 1N formic acid to obtain guanosine 3'-monophosphate as an eluate. These eluates are each concentrated, lyophilized and recrystallized from water to separate the desired 2'-GMP and 3'-GMP.

Workup

  1. customcan be obtained in the following manner in accordance with the method of Brown and Todd [D

Sources & evidence

ORD record
ord-da21917c82c64cb3a8acf549c4ed60bd
Source dataset
uspto-grants-1986_11
Patent number
US04621076

Reaction notes

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