glucosamine tetra-O-acetate → 2-nitro-4-(3'-ethyl-2', 4', 6'-triiodophenyl)-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine

HRID 1976508Notes

Reaction equation

HRID 1976508 reaction equation
[C:1]([O:4][CH:5]1[O:19][C@H:18]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[C@@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@H:8]([O:9][C:10](=[O:12])[CH3:11])[C@H:6]1[NH2:7])(=[O:3])[CH3:2].[I:25][C:26]1[C:31]([CH2:32][CH3:33])=[C:30]([I:34])[CH:29]=[C:28]([I:35])[C:27]=1[C:36]1[CH:41]=[CH:40][C:39]([C:42](Cl)=[O:43])=[C:38]([N+:45]([O-:47])=[O:46])[CH:37]=1>>[N+:45]([C:38]1[CH:37]=[C:36]([C:27]2[C:28]([I:35])=[CH:29][C:30]([I:34])=[C:31]([CH2:32][CH3:33])[C:26]=2[I:25])[CH:41]=[CH:40][C:39]=1[C:42]([C:5]1([O:19][C@H:18]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[C@@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@H:8]([O:9][C:10](=[O:12])[CH3:11])[C@H:6]1[NH2:7])[O:4][C:1](=[O:3])[CH3:2])=[O:43])([O-:47])=[O:46]

Participants

3

Reactant 2

HCID 13059363glucosamine tetra-O-acetateHCID 223419942',4',6'-Triiodo-3'-ethyl-3-nitrobiphenyl-4-carbonyl chloride

Product 1

HCID 865835212-nitro-4-(3'-ethyl-2', 4', 6'-triiodophenyl)-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine

Procedure

1,3,4,6-tetra-O-acetyl-D-glucosamine (9) is reacted with 2′, 4′, 6′-triiodo-3′-ethyl-3-nitrobiphenyl-4-carbonyl chloride (14) to yield 2-nitro-4-(3′-ethyl-2′, 4′, 6′-triiodophenyl)-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (15).

Sources & evidence

ORD record
ord-8cb346ec5d5c48a7b9a8e3caa8a041a9
Source dataset
uspto-grants-2001_05
Patent number
US06226352B1

Reaction notes

Loading…