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 octadecyl-oleamide

HRID 1636273Notes

Reaction equation

HRID 1636273 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([NH2:53])[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][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[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:54]([O:58][C:59]([NH:61][C@H:62]([C:64]([NH:66][C@H:67]([C:69](O)=[O:70])[CH3:68])=[O:65])[CH3:63])=[O:60])([CH3:57])([CH3:56])[CH3:55]>ClCCl>[C:54]([O:58][C:59]([NH:61][C@H:62]([C:64]([NH:66][C@H:67]([C:69]([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([NH2:53])[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][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[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:70])[CH3:68])=[O:65])[CH3:63])=[O:60])([CH3:57])([CH3:56])[CH3:55]

Participants

4

Reactant 2

HCID 6992569N-((1,1-Dimethylethoxy)carbonyl)-L-alanyl-L-alanineHCID 131721266N-(2-glycyl-amino-2-deoxy-beta-D-glucopyranosyl)-N-octadecyl-oleamide

Product 1

HCID 131721265N-[2-(N-tert-Butyloxycarbonyl-L-alanyl-L-alanyl-glycyl)-amino-2-deoxy-beta-D-glucopyranosyl]-N octadecyl-oleamideYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

from N-(2-glycyl-amino-2-deoxy-β-D-glucopyranosyl)-N-octadecyl-oleamide and N-tert-butyloxycarbonyl-L-alanyl-L-alanine. Yield 55%. [α]D =+10.3° (c=0.85, dichloromethane).

Sources & evidence

ORD record
ord-72d36cd20f904910825f8b28530b54af
Source dataset
uspto-grants-2000_03
Patent number
US06034055

Reaction notes

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