(2R,3R,4R,5R)-4-acetyloxy-5-(acetyloxymethyl)-2-[2-iodo-6-(methoxyamino)purin-9-yl]oxolan-3-yl acetate → (4S,2R,3R,5R)-5-(hydroxymethyl)-2-[2-iodo-6-(methoxyamino)purin-9-yl]oxolane-3,4-diol

HRID 895101

Reaktionsgleichung

Reaktionsgleichung von HRID 895101
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH2:14][O:15]C(=O)C)[O:7][C@H:6]1[N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][C:22]([I:31])=[N:23][C:24]=2[NH:28][O:29][CH3:30])(=O)C>N>[OH:15][CH2:14][C@H:8]1[O:7][C@@H:6]([N:19]2[CH:27]=[N:26][C:25]3[C:20]2=[N:21][C:22]([I:31])=[N:23][C:24]=3[NH:28][O:29][CH3:30])[C@H:5]([OH:4])[C@@H:9]1[OH:10]

Komponenten

3

Edukt 1

HCID 16115476(2R,3R,4R,5R)-4-acetyloxy-5-(acetyloxymethyl)-2-[2-iodo-6-(methoxyamino)purin-9-yl]oxolan-3-yl acetate

Produkt 1

HCID 16115751(4S,2R,3R,5R)-5-(hydroxymethyl)-2-[2-iodo-6-(methoxyamino)purin-9-yl]oxolane-3,4-diol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 222AmmoniaLösungsmittel

Versuchsvorschrift

Methanolic ammonia (30 mL) was added to (2R,3R,4R,5R)-4-acetyloxy-5-(acetyloxymethyl)-2-[2-iodo-6-(methoxyamino)purin-9-yl]oxolan-3-yl acetate (3.03 mmol). The mixture was allowed to stand at room temperature for 96 hours, then solvent was removed in vacuo and the residue chromatographed on a flash silica gel column eluting with CHCl3—CH3OH (97:3) to give the compound of formula (5), (4S,2R,3R,5R)-5-(hydroxymethyl)-2-[2-iodo-6-(methoxyamino)purin-9-yl]oxolane-3,4-diol, which was crystallized from acetonitrile,.

Aufarbeitung

  1. customsolvent was removed in vacuo
  2. customthe residue chromatographed on a flash silica gel column
  3. washeluting with CHCl3—CH3OH (97:3)

Quellen und Nachweise

ORD-Eintrag
ord-726c5adf9f45466eb96edaecf7bb936b
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06914053B2

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