4-Methylphenylhydrazine monohydrochloride → Sophorose

HRID 1653933Notes

Reaction equation

HRID 1653933 reaction equation
C([O-])(=O)C.[Na+].Cl.C1(C)C=CC(NN)=CC=1.[O:16]=[CH:17][C@@H:18]([C@H:20]([C@@H:22]([C@@H:24]([CH2:26][OH:27])[OH:25])[OH:23])[OH:21])[OH:19].[O:28]=[CH:29][C:30]([C@H:32]([C@@H:34]([C@@H:36]([CH2:38][OH:39])[OH:37])[OH:35])[OH:33])=O.C1(C)C=CC(NN=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=CC=1>O>[C@@H:26]1([O:27][C@H:30]([C@H:32]([C@@H:34]([C@@H:36]([CH2:38][OH:39])[OH:37])[OH:35])[OH:33])[CH:29]=[O:28])[O:19][C@H:18]([CH2:17][OH:16])[C@@H:20]([OH:21])[C@H:22]([OH:23])[C@H:24]1[OH:25]

Participants

7

Reactant 5

HCID 125044-Methylphenylhydrazine monohydrochlorideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal2×HCID 159630D-GlucosoneHCID 517045Sodium AcetateHCID 676372172-O-beta-D-glucopyranosyl-D-glucose p-tolylhydrazone

Product 1

HCID 92797Sophorose

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
70 °C

Procedure

This oligosaccharide (5 μmol), sodium acetate (10 μmol) and p-tolylhydrazine hydrochloride (30 μmol) were dissolved in 0.15 mL water in a small vial (Pierce reacti-vial, 0.2 mL capacity, with Tuf-bond Teflon-silicone cap seals). The vial was sealed under argon and warmed on a heating block to 70° C. for 6 hours; the solution became yellow over time and gave a yellow crystalline precipitate, which increased upon cooling to room temperature overnight. The water-insoluble material was the cleavage product, glucose p-tolylosazone (D-arabino-hexos-2-ulose p-tolylosazone). The water soluble fraction contained 2-O-β-D-glucopyranosyl-D-glucose p-tolylhydrazone, and small amounts of D-glucose and the starting oligosaccharide.

Workup

  1. customThe vial was sealed under argon
  2. customgave a yellow crystalline precipitate, which
  3. temperatureincreased
  4. temperatureupon cooling to room temperature overnight

Sources & evidence

ORD record
ord-f37304050ec04e2f838232fdd37efa1b
Source dataset
uspto-grants-1995_04
Patent number
US05403927

Reaction notes

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