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Diethyl Ether → N3-Benzyloxymethyl-5'-O-tert-butyldiphenylsilylthymidine

HRID 429951
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 429951
[Si:1]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:33]=[C:31]([CH3:32])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[CH2:22][C@@H:21]1[OH:34])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Cl[CH2:45][O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.CCOCC>C(Cl)Cl>[CH2:47]([O:46][CH2:45][N:28]1[C:29](=[O:30])[C:31]([CH3:32])=[CH:33][N:25]([C@@H:23]2[O:24][C@H:20]([CH2:19][O:18][Si:1]([C:14]([CH3:15])([CH3:17])[CH3:16])([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C@@H:21]([OH:34])[CH2:22]2)[C:26]1=[O:27])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 137983Benzyl chloromethyl etherHCID 118128465'-O-tert-Butyldiphenylsilyl-thymidine

Produkt 1

HCID 10483731N3-Benzyloxymethyl-5'-O-tert-butyldiphenylsilylthymidineAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2 (117.0 g, 243.8 mmol) and Hunig's base (diisopropylethylamine, 63.0 g, 487.5 mmol) in CH2Cl2 (400 mL) at 23° C. was added a solution of benzyl chloromethyl ether (40.7 g, 260.0 mmol) over a 15 min. period. The resultant mixture was maintained at 23° C. and stirred for 14 h. Ether (1 L) was added to the mixture and the ethereal solution was washed with 10% aqueous HCl (1×100 mL) and H2O (200 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CH2Cl2/AcOEt 40:1 then 10:1) to yield 128.9 g (88%) of 3 as a white solid. Rf(CH2Cl2/AcOEt 10:1) 0.31. 1H-NMR (CDCl3): 1.10 (s, 9H, C-Me3), 1.65 (s, 3H, 5-Me), 2.16 (m, 1H, 2′-Hβ), 2.41 (m, 1H, 2′-Hβ), 2.53 (br s, 1H 3′-OH), 3.84 (d, 1H, J=8.8 Hz, 5′-CHH), 3.98 (d, 1H, J=8.8 Hz, 5′-CHH), 4.01 (s, 1H, 4′-H), 6.64 (br s, 1H, 3′-H), 4.70 (s, 2H, OCH2Ph), 5.50 (s, 2H, NCH2O), 6.41 (dd, 1H, J=8.0, 5.8 Hz, 1′-H), 7.20-7.50 (m, 13H, aromatic-H), 7.65-7.69 (m, 3H, 6-H and aromatic-H). 13C-NMR (CDCl3): 12.86 (−5-CH3), 19.45 (+, C-Me3), 27.09 (−, C-Me3), 41.16 (+, 2′-C), 64.25 (+, 5′-C), 70.70 (+, O—C—Ph), 71.97 (−, 4′-C), 72.29 (+, N—C—C), 85.51 (−, 3′-C), 87.20 (−, 1′-C), 110.47 (+, 5-C), 127.72, 128.08, 128.36 (−, aromatic-C), 130.25 (−, 6-C), 132.42, 133.00 (+, aromatic-C) 134.39, 135.37, 135.62 (−, aromatic-C), 137.95 (+, aromatic-C), 151.01 (+, 2-C), 163.68 (+, 4-C).

Aufarbeitung

  1. washthe ethereal solution was washed with 10% aqueous HCl (1×100 mL) and H2O (200 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (CH2Cl2/AcOEt 40:1

Quellen und Nachweise

ORD-Eintrag
ord-c56e464a27fc4ec194eae5e57bda96fa
Quelldatensatz
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06320040B1

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