(-)-Mandelic acid → HCID 131713953, compound

HRID 1633290Notes

Reaction equation

HRID 1633290 reaction equation
[NH2:1][C@@H:2]1[C@@H:6]([C:7]([OH:9])=[O:8])[O:5][C@@H:4]([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[NH:19][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@H:3]1[OH:28].O=C1[O:34][C:33](=O)[CH:32]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[O:31]1.C(O)(=O)[C@@H](C1C=CC=CC=1)O>>[C:20]([NH:19][C:15]1[N:14]=[CH:13][N:12]=[C:11]2[C:16]=1[N:17]=[CH:18][N:10]2[C@@H:4]1[O:5][C@H:6]([C:7]([OH:9])=[O:8])[C@@H:2]([NH:1][C:33](=[O:34])[C@@H:32]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[OH:31])[C@H:3]1[OH:28])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 11914(-)-Mandelic acidHCID 156023925-Phenyl-1,3-dioxolane-2,4-dioneHCID 538540083-amino-1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-beta-D-ribofuranuronic acid

Product 1

HCID 131713953HCID 131713953, compoundYield 74.1%

Procedure

1-(6-Benzoylamino-9H-purin-9-yl)-3-D-mandelylamino-1,3-dideoxy-β-D-ribofuranuronic acid (300 mg) was prepared by reacting 1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-3-amino-β-D-ribofuranuronic acid (300 mg) prepared in Example 1 with 2,4-dioxo-5-phenyl-1,3-dioxolane (253 mg), prepared from D-mandelic acid, according to a similar manner to that of Example 5, mp. 223°-227° C. (dec.).

Sources & evidence

ORD record
ord-dd6f5b9bb2414c3e9ca29171143bd199
Source dataset
uspto-grants-1984_10
Patent number
US04479942

Reaction notes

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