HCID 131719637, compound → HCID 131719635, compound

HRID 2395230Notes

Reaction equation

HRID 2395230 reaction equation
[CH:1]1[C@H:6]([NH2:7])[C@H:5]([OH:8])[C@@H:4]([OH:9])[C@H:3]([OH:10])[C:2]=1[CH2:11][OH:12].[CH2:13]1[O:19][C@@H:18]2[O:20][C@H:14]1[C@@H:15]([OH:23])[C@H:16]([OH:22])[C@H:17]2[OH:21]>Cl>[CH:1]1[C@H:6]([NH2:7])[C@H:5]([OH:8])[C@@H:4]([OH:9])[C@H:3]([OH:10])[C:2]=1[CH2:11][OH:12].[O:19]=[CH:13][C@@H:14]([C@H:15]([C@@H:16]([C@@H:17]([CH2:18][OH:8])[OH:21])[OH:22])[OH:23])[OH:20]

Participants

3

Reactant 1

HCID 131719637HCID 131719637, compound2×

Product 1

HCID 131719635HCID 131719635, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1,6-anhydro-2-deoxy-2-[1D-(1N,2,4/3)-5-C-hydroxymethyl-2,3,4-trihydroxy-5-cyclohexen-1-yl)amino]-β-D-glucopyranose (compound 5) (152.5 mg, 0.47 mmol) was heated at 100° C. in 2N HCl solution for 4 days. Solvent was removed by co-evaporation with water and the residue was purified by chromatography on an latrobeads column (Iatron Laboratories, Japan) using chloroform:methanol:water, (65:38:3) as eluent to provide 2-deoxy-2-[ID-(1N,2,4/3)-(5-C-hydroxymethyl-2,3,4-trihydroxy-5-cyclohexen-1-yl)amino]-D-glucopyranose hydrochloride (compound 6) after lyophilization (116 mg, 65%).

Workup

  1. customSolvent was removed by co-evaporation with water
  2. customthe residue was purified by chromatography on an latrobeads column (Iatron Laboratories, Japan)

Sources & evidence

ORD record
ord-f1b27c4359df410794ec9f737d95f33a
Source dataset
uspto-grants-1998_09
Patent number
US05814616

Reaction notes

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