Triethylamine → N-(9-((2R,4S,5R)-5-((Tert-butyldimethylsilyloxy)methyl)-4-hydroxytetrahydrofuran-2-YL)-9H-purin-6-YL)benzamide

HRID 55552

Reaktionsgleichung

Reaktionsgleichung von HRID 55552
C(OC[C@H]1O[C@@]([SiH](C)C)(N2C=C(C)C(=O)NC2=O)C[C@@H]1O)(C)(C)C.[C:25]([NH:33][C:34]1[C:35]2[N:36]=[CH:37][N:38]([C:47]=2[N:48]=[CH:49][N:50]=1)[C@@H:39]1[O:46][C@H:43]([CH2:44][OH:45])[C@@H:41]([OH:42])[CH2:40]1)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C.[C:58]([Si:62]([CH3:65])([CH3:64])Cl)([CH3:61])([CH3:60])[CH3:59]>CN(C)C=O.ClCCl.C(O)C>[C:25]([NH:33][C:34]1[C:35]2[N:36]=[CH:37][N:38]([C:47]=2[N:48]=[CH:49][N:50]=1)[C@@H:39]1[O:46][C@H:43]([CH2:44][O:45][Si:62]([C:58]([CH3:61])([CH3:60])[CH3:59])([CH3:65])[CH3:64])[C@@H:41]([OH:42])[CH2:40]1)(=[O:32])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 107558N-benzoyl-2'-deoxyadenosineHCID 573497865'-O-tertbutyldimethylsilylthymidine

Produkt 1

HCID 13833804N-(9-((2R,4S,5R)-5-((Tert-butyldimethylsilyloxy)methyl)-4-hydroxytetrahydrofuran-2-YL)-9H-purin-6-YL)benzamideAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 21584144Dichloromethane ethanolLösungsmittel

Versuchsvorschrift

N6 -Benzoyl-5'-O-tert-butyldimethylsilyl-2'-deoxyadenosine (Compound 5, Table I) was prepared by a procedure similar to that used to prepare the 5'-O-tertbutyldimethylsilylthymidine, as described in Example 1, except that N6 -benzoyl-2'-deoxyadenosine (10 g, 26.9 mmole), 4-N,N-dimethylaminopyridine (0.86 g, 7.0 mmole), triethylamine (3.6 g, 4.96 ml, 35.4 mmole) and tert-butyldimethylchlorosilane (5.33 g, 35.4 mmole) were dissolved in 100 ml dry N,N-dimethylformamide. The reaction was allowed to stir for 2 hours before being worked up as described in Example 1. Chromatography was performed using dichloromethane/ethanol (20/1) as eluent to yield 9.6 g N6 -benzoyl-5'-O-tert-butyldimethylsilyl-2'-deoxyadenosine as a white foam (73% yield).

Aufarbeitung

  1. customN6 -Benzoyl-5'-O-tert-butyldimethylsilyl-2'-deoxyadenosine (Compound 5, Table I) was prepared by a procedure similar to

Quellen und Nachweise

ORD-Eintrag
ord-9958ce6b270e40cb8daea0d110d8994c
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05625050

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