N-carbobenzyloxyalanine → 1-(6-Benzoylamino-9H-purin-9-yl)-3-(N-benzyloxycarbonyl-L-alanylamino)-1,3-dideoxy-beta-D-ribofuranuronic acid

HRID 1633282Notes

Reaction equation

HRID 1633282 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].[CH2:29]([O:36][C:37]([NH:39][C@H:40]([C:42](O)=[O:43])[CH3:41])=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[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:42](=[O:43])[C@H:40]([CH3:41])[NH:39][C:37]([O:36][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:38])[C@H:3]1[OH:28])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 736104N-carbobenzyloxyalanineHCID 538540083-amino-1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-beta-D-ribofuranuronic acid

Product 1

HCID 704656031-(6-Benzoylamino-9H-purin-9-yl)-3-(N-benzyloxycarbonyl-L-alanylamino)-1,3-dideoxy-beta-D-ribofuranuronic acidYield 67.4%

Procedure

1-(6-Benzoylamino-9H-purin-9-yl)-3-(N-benzyloxycarbonyl-L-alanylamino)-1,3-dideoxy-β-D-ribofuranuronic acid (310 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 N-hydroxysuccinimide ester of N-benzyloxycarbonyl-L-alanine (300 mg) according to a similar manner to that of Example 5, mp. 154°-156° C.

Sources & evidence

ORD record
ord-a47e7db65ae8435b9ff69566e37c9648
Source dataset
uspto-grants-1984_10
Patent number
US04479942

Reaction notes

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