N-(Benzyloxycarbonyl)-L-serine → N-[2-(N-Carbobenzoxy-L-seryl-glycyl)-amino-2-deoxy-beta-D-glucopyranosyl]-N-tetradecyl-dodecanamide

HRID 1636244Notes

Reaction equation

HRID 1636244 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([NH2:43])[N:15]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:16](=[O:28])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:4].[C:44]([NH:54][C@H:55]([C:58](O)=[O:59])[CH2:56][OH:57])([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45]>ClCCl>[C:44]([NH:54][C@H:55]([C:56]([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([NH2:43])[N:15]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:16](=[O:28])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:4])=[O:57])[CH2:58][OH:59])([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45]

Participants

4

Reactant 2

HCID 100310N-(Benzyloxycarbonyl)-L-serineHCID 131721235N-(2-glycyl-amino-2-deoxy-beta-D-glucopyranosyl)-N-tetradecyl-dodecanamide

Product 1

HCID 131721239N-[2-(N-Carbobenzoxy-L-seryl-glycyl)-amino-2-deoxy-beta-D-glucopyranosyl]-N-tetradecyl-dodecanamideYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

from N-(2-glycyl-amino-2-deoxy-β-D-glucopyranosyl)-N-tetradecyl-dodecanamide and N-carbobenzoxy-L-serine. Yield 76%. [α]D =+20.3° (c=0.89, dichloromethane). m.p. 87-89°.

Sources & evidence

ORD record
ord-e34557ed20084340812fdd2d2cf91dd9
Source dataset
uspto-grants-2000_03
Patent number
US06034055

Reaction notes

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