Hydrogen Peroxide → HCID 68438823, compound

HRID 713719Notes

Reaction equation

HRID 713719 reaction equation
[CH3:1][C@@:2]1([OH:20])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[C:19]2[N:18]=C[N:16]=[C:14]([NH2:15])[C:13]=2[N:12]=[CH:11]1.OO.C1C=CC(CBr)=CC=1.[OH-].[Na+].N.CO.[N:36]([O-])=O.[Na+]>[H][H].[Pd].O.CC(O)=O.CO.CCO.CC(N(C)C)=O>[CH3:1][C@@:2]1([OH:20])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[C:19]2[N:18]=[N:36][N:16]=[C:14]([NH2:15])[C:13]=2[N:12]=[CH:11]1

Participants

13

Reactant 6

HCID 784Hydrogen PeroxideHCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 5009002'-C-methyladenosineHCID 21705897Ammonia methanolHCID 23668193Sodium Nitrite

Product 1

HCID 68438823HCID 68438823, compound

Reagents, catalysts & solvents 6

HCID 178506449HCID 178506449, compoundCatalystHCID 176Acetic AcidSolvent2×HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 31374DimethylacetamideSolvent

Procedure

(Synthesis according to the procedure of J. A. Montgomery, Nucleic Acid Chemistry, 1978, Part II, 681-685 starting with 2′-C-methyladenosine.) Step 1: H2O2, AcOH, 80%; Step 2: BnBr, DMAc, Step 3: NaOH, H2O, EtOH, 30%, Step 4: NH3/MeOH, 80° C., 2 days, 60%; Step 5: H2/Pd/C, 3 atm, MeOH, 30% Step 6: NaNO2, AcOH, H2O, 50%.

Workup

  1. custom(Synthesis

Sources & evidence

ORD record
ord-1fa31e07ed4c415d82536001445400de
Source dataset
uspto-grants-2015_11
Patent number
US09186369B2

Reaction notes

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