HCID 178476368, compound → HCID 178476372, compound

HRID 991146Notes

Reaction equation

HRID 991146 reaction equation
[CH3:1][C:2]1([CH3:40])[CH2:7][C:6](=[O:8])[C:5](=[C:9]([NH:11][C@@H:12]2[C@@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@H:24]([O:30][C:31](=[O:33])[CH3:32])[C@@H:23]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[O:22][C@@H:13]2[O:14]CC2C=CC=CC=2)[CH3:10])[C:4](=[O:39])[CH2:3]1>CO.[Pd]>[CH3:1][C:2]1([CH3:40])[CH2:3][C:4](=[O:39])[C:5](=[C:9]([NH:11][C@@H:12]2[C@@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@H:24]([O:30][C:31](=[O:33])[CH3:32])[C@@H:23]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[O:22][C@@H:13]2[OH:14])[CH3:10])[C:6](=[O:8])[CH2:7]1

Participants

4

Reactant 1

HCID 178476368HCID 178476368, compound

Product 1

HCID 178476372HCID 178476372, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl 2-Deoxy-2-[1-(4,4-dimethyl-2,6-dioxo-cyclohex-1-ylidene)ethylamino]-3,4,6-tri-O-acetyl-α-D-glucopyranoside (11) (100 mg, 0.17 mmol) was dissolved in MeOH (5 ml) and hydrogenated over Pd/C (10%) (20 mg) overnight. The suspension was filtered, and the filtrate was evaporated to give 2-Deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylamino]-3,4,6-tri-O-acetyl-α-D-glucopyranose (12) (75 mg, 90%).

Workup

  1. filtrationThe suspension was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-5469acc6263e4a4c8323b623c4338050
Source dataset
uspto-grants-2002_10
Patent number
US06462183B1

Reaction notes

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