N-((1,1-Dimethylethoxy)carbonyl)-L-alanyl-L-alanine → N-[2-(N-tert-Butyloxycarbonyl-L-alanyl-L-alanyl-glycyl)-amino-2-deoxy-beta-D-glucopyranosyl]-N-tetradecyl-oleamide

HRID 1075608

Reaction equation

HRID 1075608 reaction equation
[NH2:1][CH2:2][C:3]([C@@H:5]1[C@@H:10]([OH:11])[C@H:9]([OH:12])[C@@H:8]([CH2:13][OH:14])[O:7][C@@:6]1([NH2:49])[N:15]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[C:16](=[O:34])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:4].[C:50]([O:54][C:55]([NH:57][C@H:58]([C:60]([NH:62][C@H:63]([C:65](O)=[O:66])[CH3:64])=[O:61])[CH3:59])=[O:56])([CH3:53])([CH3:52])[CH3:51]>O1CCCC1>[C:50]([O:54][C:55]([NH:57][C@H:58]([C:60]([NH:62][C@H:63]([C:65]([NH:1][CH2:2][C:3]([C@@H:5]1[C@@H:10]([OH:11])[C@H:9]([OH:12])[C@@H:8]([CH2:13][OH:14])[O:7][C@@:6]1([NH2:49])[N:15]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[C:16](=[O:34])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:4])=[O:66])[CH3:64])=[O:61])[CH3:59])=[O:56])([CH3:53])([CH3:52])[CH3:51]

Participants

4

Reactant 2

HCID 6992569N-((1,1-Dimethylethoxy)carbonyl)-L-alanyl-L-alanineHCID 131721258N-(2-glycyl-amino-2-deoxy-beta-glucopyranosyl)-N-tetradecyl-oleamide

Product 1

HCID 131721259N-[2-(N-tert-Butyloxycarbonyl-L-alanyl-L-alanyl-glycyl)-amino-2-deoxy-beta-D-glucopyranosyl]-N-tetradecyl-oleamideYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

from N-(2-glycyl-amino-2-deoxy-β-D-glucopyranosyl)-N-tetradecyl-oleamide and N-tert-butyloxycarbonyl-L-alanyl-L-alanine. Yield 71%. [α]D =+7.4° (c=0.82, tetrahydrofuran).

Sources & evidence

ORD record
ord-6508b661d70842bea118aee166f323f1
Source dataset
uspto-grants-1999_05
Patent number
US05905071

Linked notes

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