5-amino-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)imidazole-4-carboxylic acid → HCID 178516781, compound

HRID 965373Notes

Reaction equation

HRID 965373 reaction equation
[CH:1]1[N:5]([C@@H:6]2[O:10][C@H:9]([CH2:11][OH:12])[C@@H:8]([OH:13])[C@H:7]2[OH:14])[C:4]2[N:15]=[CH:16][NH:17][CH2:18][C@@H:19]([OH:20])[C:3]=2[N:2]=1.NC1N([C@@H]2O[C@H](COC(=O)C)[C@@H](OC(=O)C)[C@H]2OC(=O)C)C=NC=1C(O)=O>>[C@@H:6]1([N:5]2[C:4]3[N:15]=[CH:16][NH:17][CH2:18][C:19](=[O:20])[C:3]=3[N:2]=[CH:1]2)[O:10][C@H:9]([CH2:11][OH:12])[C@@H:8]([OH:13])[C@H:7]1[OH:14]

Participants

3

Reactant 2

HCID 118111085-amino-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)imidazole-4-carboxylic acidHCID 178521061HCID 178521061, compound2×

Product 1

HCID 178516781HCID 178516781, compound

Procedure

As another method for the synthesis of coformycin, there is also a known process of producing coformycin in which 5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carboxylic acid is used as the starting material, and is processed by multi-stage reactions to form an intermediate, 3-(β-D-ribofuranosyl)-6,7-dihydroimidazo[4,5-d][1,3]diazepin-8(3H)-one, followed by reducing the latter intermediate [see, H. J. Thomas et al.; "Nucleosides & Nucleotides" 5, No. 4, pp.431-439 (1986)]

Sources & evidence

ORD record
ord-02bc44303fd84cc39c5d7001a8846c81
Source dataset
uspto-grants-1998_06
Patent number
US05773607

Reaction notes

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