8-(3'-Benzyloxybiphenyl-4-ylmethyl-amino)-2',3',5'-tris-o-(tert-butyldimethylsilyl)adenosine → 2',3',5'-Tris-o-(tert-butyl-dimethylsilyl)-8-(3'-hydroxybiphenyl-4-ylmethylamino)-adenosine

HRID 1713297Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1713297
C([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][NH:22][C:23]3[N:24]([C:55]4[N:56]=[CH:57][N:58]=[C:59]([NH2:62])[C:60]=4[N:61]=3)[C@@H:25]3[O:54][C@H:44]([CH2:45][O:46][Si:47]([C:50]([CH3:53])([CH3:52])[CH3:51])([CH3:49])[CH3:48])[C@@H:35]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[C@H:26]3[O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>[Pd].C(OCC)(=O)C>[Si:28]([O:27][C@@H:26]1[C@H:35]([O:36][Si:37]([C:40]([CH3:41])([CH3:42])[CH3:43])([CH3:39])[CH3:38])[C@@H:44]([CH2:45][O:46][Si:47]([C:50]([CH3:51])([CH3:52])[CH3:53])([CH3:48])[CH3:49])[O:54][C@H:25]1[N:24]1[C:55]2[N:56]=[CH:57][N:58]=[C:59]([NH2:62])[C:60]=2[N:61]=[C:23]1[NH:22][CH2:21][C:18]1[CH:17]=[CH:16][C:15]([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[CH:10]=2)=[CH:20][CH:19]=1)([C:31]([CH3:33])([CH3:34])[CH3:32])([CH3:29])[CH3:30]

Komponenten

4

Edukt 1

HCID 674544418-(3'-Benzyloxybiphenyl-4-ylmethyl-amino)-2',3',5'-tris-o-(tert-butyldimethylsilyl)adenosine

Produkt 1

HCID 674557002',3',5'-Tris-o-(tert-butyl-dimethylsilyl)-8-(3'-hydroxybiphenyl-4-ylmethylamino)-adenosineAusbeute 95,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 8-(3′-benzyloxybiphenyl-4-ylmethyl-amino)-2′,3′,5′-tris-O-(tert-butyldimethylsilyl)adenosine (0.713 g) and 10% palladium on carbon (55.4 wt % H2O, 0.480 g) in ethyl acetate (11 mL) was stirred at room temperature for 23 hours under a hydrogen atmosphere. The insoluble material was filtered out and the filtrate was concentrated under reduced pressure to give the title compound (0.615 g).

Aufarbeitung

  1. filtrationThe insoluble material was filtered out
  2. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9e156b14a62b4cb8859616c7f441519c
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795236B2

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