Methanol → HCID 178504346, Verbindung

HRID 370296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 370296
[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]

Komponenten

6

Edukt 2

HCID 887MethanolHCID 178504348HCID 178504348, Verbindung

Produkt 1

HCID 178504346HCID 178504346, VerbindungAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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%).

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-d68b0154ed5149d0bede9679941ac961
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06140496

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