(3S)-4-(tert-butoxy)-3-{[(tert-butoxy)carbonyl]amino}-4-oxobutanoic acid → N-[2-(N-tert-Butyloxycarbonyl-O-tert-butyl-L-aspartyl-L-alanyl)-amino-2-deoxy-beta-D-glucopyranosyl]-N-octadecyl-oleamide

HRID 1075615Notes

Reaction equation

HRID 1075615 reaction equation
[NH2:1][C@H:2]([C:4]([C@@H:6]1[C@@H:11]([OH:12])[C@H:10]([OH:13])[C@@H:9]([CH2:14][OH:15])[O:8][C@@:7]1([NH2:54])[N:16]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[C:17](=[O:35])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]\[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:5])[CH3:3].[C:55]([O:59][C:60]([NH:62][C@H:63]([C:68]([O:70]C(C)(C)C)=O)[CH2:64][C:65]([OH:67])=[O:66])=[O:61])([CH3:58])([CH3:57])[CH3:56]>ClCCl>[C:55]([O:59][C:60]([NH:62][C@H:63]([C:68]([NH:1][C@H:2]([C:4]([C@@H:6]1[C@@H:11]([OH:12])[C@H:10]([OH:13])[C@@H:9]([CH2:14][OH:15])[O:8][C@@:7]1([NH2:54])[N:16]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[C:17](=[O:35])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]\[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:5])[CH3:3])=[O:70])[CH2:64][C:65](=[O:66])[O:67][C:6]([CH3:11])([CH3:7])[CH3:4])=[O:61])([CH3:56])([CH3:57])[CH3:58]

Participants

4

Reactant 2

HCID 7010517(3S)-4-(tert-butoxy)-3-{[(tert-butoxy)carbonyl]amino}-4-oxobutanoic acidHCID 86755189N-(2-L-alanyl-amino-2-deoxy-beta-D-glucopyranosyl)-N-octadecyl-oleamide

Product 1

HCID 131721267N-[2-(N-tert-Butyloxycarbonyl-O-tert-butyl-L-aspartyl-L-alanyl)-amino-2-deoxy-beta-D-glucopyranosyl]-N-octadecyl-oleamideYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

from N-(2-L-alanyl-amino-2-deoxy-β-D-glucopyranosyl)-N-octadecyl-oleamide and N-tert-butyloxycarbonyl-O-tert-butyl-L-aspartic acid. Yield 27%. [α]D =-1.5° (c=0.55, dichloromethane).

Sources & evidence

ORD record
ord-9bd83a5aff4e4c3faed06be4adcf995d
Source dataset
uspto-grants-1999_05
Patent number
US05905071

Reaction notes

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