Ammonium Hydroxide → 1-(Hydroxymethyl)-5-{[4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}cyclohexane-1,2,3,4-tetrol

HRID 1650325Notes

Reaction equation

HRID 1650325 reaction equation
[CH2:1]1[C@:6]([OH:9])([CH2:7][OH:8])[C@@H:5]([O:10][C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H:4]([OH:22])[C@@H:3]([OH:23])[C@H:2]1[NH:24][C@@H:25]1[C@H:30]([OH:31])[C@@H:29]([OH:32])[C@H:28]([OH:33])[C:27]([CH2:34][OH:35])=[CH:26]1.[NH4+].[OH-]>N1C=CC=CC=1>[CH2:1]1[C:6]([OH:9])([CH2:7][OH:8])[CH:5]([OH:10])[CH:4]([OH:22])[CH:3]([OH:23])[CH:2]1[NH:24][CH:25]1[CH:30]([OH:31])[CH:29]([OH:32])[CH:28]([OH:33])[C:27]([CH2:34][OH:35])=[CH:26]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 10006646HCID 10006646, compound

Product 1

HCID 1947201-(Hydroxymethyl)-5-{[4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}cyclohexane-1,2,3,4-tetrol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

One hundred grams of the crude powder containing validamycin G and validoxylamine G obtained in Example 1a) was submitted to column chromatography on Dowex 1×2 (OH- form, manufactured by Dow Chemicals; 1.8L), eluted with water to give validoxylamine G-containing fractions (eluate fractions 3-5 L; abbreviated as eluate fraction I' hereafter) and validamycin G-containing fractions (eluate fractions 6-8 L; abbreviated as `eluate fraction II` hereafer). The eluate fraction I and the eluate fraction II were separately concentrated to dryness to give 2.7 and 3.0 g of a crude powder, respectively. The crude powder from the eluate fraction I (2.7 g) was submitted to column chromatography on Dowex 50W x 8 (pyridine form, manufactured by Dow Chemicals Co.; 200 mL) and eluted with 0.2 M pyridine-acetate buffer (pH 6.0). In succession to the fractions containing validoxylamine B and validamycin D (eluate fractions 100-420 mL), validoxylamine G-containing fractions (eluate fractions 520-1140 mL) were eluted. The validoxylamine G-containing eluate fractions were concentrated to dryness under reduced pressure, to give a white powder (0.8 g) of validoxylamine G.

Workup

  1. additioncontaining fractions (eluate fractions 3-5 L
  2. concentrationThe eluate fraction I and the eluate fraction II were separately concentrated to dryness
  3. customto give 2.7 and 3.0 g of a crude powder
  4. washeluted with 0.2 M pyridine-acetate buffer (pH 6.0)
  5. additionIn succession to the fractions containing validoxylamine B and validamycin D (eluate fractions 100-420 mL), validoxylamine G-
  6. additioncontaining fractions (eluate fractions 520-1140 mL)
  7. washwere eluted
  8. additionThe validoxylamine G-containing eluate fractions
  9. concentrationwere concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-907501d2e2f44a6aad8461e4cf5b2ae8
Source dataset
uspto-grants-1990_05
Patent number
US04923975

Reaction notes

Loading…