N,N'-(7H-Purine-2,6-diyl)diacetamide → 2,6-Diacetamido-9-(Triacetyl-beta-D-Ribofuranosyl)Purine
Reaction equation
[C:1]([NH:4][C:5]1[N:13]=[C:12]2[C:8]([NH:9][CH:10]=[N:11]2)=[C:7]([NH:14][C:15](=[O:17])[CH3:16])[N:6]=1)(=[O:3])[CH3:2].[C:18]([C@@:21]1([OH:36])[C@@H:25]([CH2:26][OH:27])[O:24][C:23](Cl)([C:28](=[O:30])[CH3:29])[C@:22]1([C:33](=[O:35])[CH3:34])[OH:32])(=[O:20])[CH3:19]>>[C:1]([NH:4][C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][N:11]2[C@:23]2([C:28](=[O:30])[CH3:29])[O:24][C@H:25]([CH2:26][OH:27])[C@@:21]([C:18](=[O:20])[CH3:19])([OH:36])[C@@:22]2([C:33](=[O:35])[CH3:34])[OH:32])=[C:7]([NH:14][C:15](=[O:17])[CH3:16])[N:6]=1)(=[O:3])[CH3:2]Participants
Procedure
Generally speaking, compounds of this invention are prepared from 2-acetamido-adenosine-5'-carboxylic acid or from the corresponding 2',3'-isopropylidene derivatives. 2-acetamido-adenosine-5'-carboxylic acid is obtained by reacting 2,6-diaminopurine sulfate with sodium hydroxide to obtain 2,6-diaminopurine which is then reacted with acetic anhydride to yield 2,6-diacetamidopurine, which in turn is converted to a mercuri chloride complex. The mercuri chloride complex of 2,6-diacetamidopurine is then reacted with triacetyl D-ribofuranosyl chloride to obtain 2,6diacetamido-9-(triacetyl-β-D-ribofuranosyl) purine, which is then converted to the corresponding 2-acetamido adenosine by treatment with methanol in the presence of ammonia. Preparation of 2-acetamido adenosine from 2,6-diaminopurine sulfate has been described by J. Davoll & B. A. Lowy [J.A.C.S., 73, 1650 (1951)]. The corresponding isopropylidene compound is obtained by reacting 2-acetamido adenosine with acetone. Potassium permanganate oxidation affords the corresponding 5'-carboxylic acid.
Sources & evidence
- ORD record
- ord-f500ad365b064c5fae66da82b110093b
- Source dataset
- uspto-grants-1976_11
- Patent number
- US03992531
Reaction notes
Loading…