N2,N6-Bis[(phenylmethoxy)carbonyl]-L-lysine → 1-(6-Benzoylamino-9H-purin-9-yl)-3-(Nalpha,Nepsilon-dibenzyloxycarbonyl-L-lysylamino)-1,3-dideoxy-beta-D-ribofuranuronic acid

HRID 1633280Notes

Reaction equation

HRID 1633280 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:56](O)=[O:57])[CH2:41][CH2:42][CH2:43][CH2:44][NH:45][C:46]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:47])=[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:56](=[O:57])[C@H:40]([CH2:41][CH2:42][CH2:43][CH2:44][NH:45][C:46]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[O:47])[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 7269422N2,N6-Bis[(phenylmethoxy)carbonyl]-L-lysineHCID 538540083-amino-1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-beta-D-ribofuranuronic acid

Product 1

HCID 704660111-(6-Benzoylamino-9H-purin-9-yl)-3-(Nalpha,Nepsilon-dibenzyloxycarbonyl-L-lysylamino)-1,3-dideoxy-beta-D-ribofuranuronic acidYield 53.8%

Procedure

1-(6-Benzoylamino-9H-purin-9-yl)-3-(Nα,Nε -dibenzyloxycarbonyl-L-lysylamino)-1,3-dideoxy-β-D-ribofuranuronic acid (420 mg) was prepared by reacting 1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-3-amino-β-D-ribofuranuronic acid (384 mg) prepared in Example 1 with N-hydroxysuccinimide ester of Nα,Nε -dibenzyloxycarbonyl-L-lysine (608 mg) according to a similar manner to that of Example 5, mp. 150°-157° C. (dec.).

Sources & evidence

ORD record
ord-bb15dccb32864a30b164f06c0fb23b7d
Source dataset
uspto-grants-1984_10
Patent number
US04479942

Reaction notes

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