Methanol → HCID 135707808, compound

HRID 845036Notes

Reaction equation

HRID 845036 reaction equation
I([O-])(=O)(=O)=O.[Na+].[OH:7][CH:8](CO)[CH2:9][CH2:10][CH2:11][N:12]1[CH:20]=[N:19][C:18]2[C:17](=[O:21])[NH:16][C:15]([NH2:22])=[N:14][C:13]1=2.C(Cl)(Cl)Cl.CO>O>[NH:16]1[C:17](=[O:21])[C:18]2[N:19]=[CH:20][N:12]([CH2:11][CH2:10][CH2:9][CH:8]=[O:7])[C:13]=2[N:14]=[C:15]1[NH2:22]

Participants

6

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 23667635Sodium periodateHCID 136169459HCID 136169459, compound

Product 1

HCID 135707808HCID 135707808, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a vigorously stirred solution of 113 mg (0.53 mmole) of sodium periodate in 1.1 ml of H2O at room temperature was added 101 mg (0.4 mmole) of (±)-9-(4,5-dihydroxypentyl)guanine. After 2 hours, TLC (silica gel, 70:30:3 CHCl3 --MeOH--H2O) showed complete conversion to a faster-moving product. The white solid was collected on a filter and washed with some H2O, then with diethyl ether, to give 79 mg of white solid. Recrystallization from H2O--MeOH yielded 29 mg (33%) of white solid, m.p. not less than 300° C. By 200 MHz NMR (DMSO-d6), the material consisted of a mixture of the free aldehyde and the covalent hydrate. A similar preparation showed only the free aldehyde by NMR.

Workup

  1. customThe white solid was collected on
  2. filtrationa filter
  3. washwashed with some H2O

Sources & evidence

ORD record
ord-4d2355ace09a4a639762f765880133b3
Source dataset
uspto-grants-1988_07
Patent number
US04755516

Reaction notes

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