Methanol → HCID 178504346, compound

HRID 370296Notes

Reaction equation

HRID 370296 reaction equation
[C:1]([C@@:5]1([OH:29])[C@@H:9]([CH2:10][O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[O:8][C@@:7]([SiH:26]([CH3:28])[CH3:27])([N:16]2[C:25]3[N:24]=[CH:23][N:22]=[C:20]([NH2:21])[C:19]=3[N:18]=[CH:17]2)[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C[OH:31]>CCO.O.C(Cl)Cl>[C:1]([C@@:5]1([OH:29])[C@@H:9]([CH2:10][O:11][C:12]([CH3:15])([CH3:13])[CH3:14])[O:8][C@@:7]([SiH:26]([CH3:27])[CH3:28])([N:16]2[C:25]3[N:24]=[CH:23][N:22]=[C:20]([NH2:21]=[O:31])[C:19]=3[N:18]=[CH:17]2)[CH2:6]1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 2

HCID 887MethanolHCID 178504348HCID 178504348, compound

Product 1

HCID 178504346HCID 178504346, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3',5'-O-bis-tert.-butyldimethylsilyl-2'-deoxyadenosine (Ogilvie, K. K. (1973) Can. J. Chem. 51, 3799-3807.)(6.0 g, 12.5 mmol) in a mixture of EtOH and H2O (2.5:1) was added at RT monopermaleic acid (24 mmol). After 2 days, another 6 equiv. of monopermaleic acid were added, and the reaction continued for two weeks. Continuous monitoring (TLC on SiO2, 10% MeOH in CH2Cl2) showed that the reaction did not proceed to completion even though peracid was still detectable (KI test). After two weeks, CH2Cl2 was added, the organic phase extracted with saturated NaHCO3, and 3',5'-O-bis-tert.-butyldimethylsilyl-2'-deoxyadenosine N-oxide (3.41 g, 55%) isolated by chromatography (SiO2, EtOAc:hexane 4:1) together with starting material (2.33 g, 39%).

Workup

  1. waitthe reaction continued for two weeks
  2. waitAfter two weeks
  3. extractionthe organic phase extracted with saturated NaHCO3, and 3',5'-O-bis-tert.-butyldimethylsilyl-2'-deoxyadenosine N-oxide (3.41 g, 55%)

Sources & evidence

ORD record
ord-d68b0154ed5149d0bede9679941ac961
Source dataset
uspto-grants-2000_10
Patent number
US06140496

Reaction notes

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