(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride → HCID 178464541, compound

HRID 991152Notes

Reaction equation

HRID 991152 reaction equation
[Na].Cl.[OH:3][CH:4]1[O:12][C@H:11]([CH2:13][OH:14])[C@@H:9]([OH:10])[C@H:7]([OH:8])[C@H:5]1[NH2:6].[C:15]([CH:18]1[C:26](=[O:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][C:24]=2[N+:28]([O-:30])=[O:29])[C:19]1=[O:31])(=O)[CH3:16]>CO>[N+:28]([C:24]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:25]=1[C:26](=[O:27])[C:18](=[C:15]([NH:6][C@@H:5]1[C@@H:7]([OH:8])[C@H:9]([OH:10])[C@@H:11]([CH2:13][OH:14])[O:12][CH:4]1[OH:3])[CH3:16])[C:19]2=[O:31])([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 2723635(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochlorideHCID 27352622-Acetyl-4-nitro-1H-indene-1,3(2H)-dioneHCID 5360545Sodium

Product 1

HCID 178464541HCID 178464541, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium (126 mg, 5.47 mmol) was added to abs. methanol (50 ml) and the reaction mixture was stirred for 5 min. D-glucosamine hydrochloride (1.18 g, 5.47 mmol) was added to the resulting clear solution and the reaction mixture was stirred at room temperature for another 5 min. 2-acetyl-4-nitroindane-1,3-dion (1.91 g, 8.21 mmol) was added and the reaction mixture was stirred under reflux for 5 hours. The solution was cooled and the product was filtered off. The solid was washed with MeOH (10 ml), ether (50 ml) and dried, affording 2-Deoxy-2-[1-(4-nitro-1,3-dioxoindan-2-ylidene)ethylamino]-D-glucopyranose (22) 1.10 g, 55%).

Workup

  1. stirringthe reaction mixture was stirred
  2. temperatureunder reflux for 5 hours
  3. temperatureThe solution was cooled
  4. filtrationthe product was filtered off
  5. washThe solid was washed with MeOH (10 ml), ether (50 ml)
  6. customdried

Sources & evidence

ORD record
ord-a5d227764a8240a8aed8624ae16d1c18
Source dataset
uspto-grants-2002_10
Patent number
US06462183B1

Reaction notes

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