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

HRID 1636271Notes

Reaction equation

HRID 1636271 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:67]([O:69]C(C)(C)C)=O)[CH2:63][C:64]([OH:66])=[O:65])=[O:60])([CH3:57])([CH3:56])[CH3:55]>ClCCl>[C:54]([O:58][C:59]([NH:61][C@H:62]([C:67]([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:69])[CH2:63][C:64](=[O:65])[O:66][C:5]([CH3:10])([CH3:6])[CH3:3])=[O:60])([CH3:55])([CH3:56])[CH3:57]

Participants

4

Reactant 2

HCID 7010517(3S)-4-(tert-butoxy)-3-{[(tert-butoxy)carbonyl]amino}-4-oxobutanoic acidHCID 131721266N-(2-glycyl-amino-2-deoxy-beta-D-glucopyranosyl)-N-octadecyl-oleamide

Product 1

HCID 131721724N-[2-(N-tert-Butyloxycarbonyl-O-tert-butyl-L-aspartyl-glycyl)-amino-2-deoxy-beta-D-glucopyranosyl]-N-octadecyl-oleamideYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

from N-(2-glycyl-amino-2-deoxy-β-D-glucopyranosyl)-N-octadecyl-oleamide and N-tert-butyloxycarbonyl-O-tert-butyl-L-aspartic acid. Yield 88%. [α]D =+13.8° (c=0.93, dichloromethane).

Sources & evidence

ORD record
ord-286bd0568f224b57bd5c2f012d0b575c
Source dataset
uspto-grants-2000_03
Patent number
US06034055

Reaction notes

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