Benzaldehyde → (2S,3R,4R,5S,6S)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol

HRID 2058025

Reaktionsgleichung

Reaktionsgleichung von HRID 2058025
[CH2:1]1[C@H:6]([NH2:7])[C@@H:5]([O:8][C@H:9]2[O:14][C@H:13]([CH2:15][NH2:16])[C@@H:12]([OH:17])[C@H:11]([OH:18])[C@H:10]2[OH:19])[C@H:4]([OH:20])[C@@H:3]([O:21][C@H:22]2[O:27][C@H:26]([CH2:28][OH:29])[C@@H:25]([OH:30])[C@H:24]([NH2:31])[C@H:23]2[OH:32])[C@@H:2]1[NH2:33].OS(O)(=O)=O.Cl.C([BH3-])#N.[Na+].C(=O)C1C=CC=CC=1>O.CO.CO.C(Cl)(Cl)Cl>[CH2:1]1[C@H:6]([NH2:7])[C@@H:5]([O:8][C@@H:9]2[O:14][C@@H:13]([CH2:15][NH2:16])[C@H:12]([OH:17])[C@@H:11]([OH:18])[C@@H:10]2[OH:19])[C@H:4]([OH:20])[C@@H:3]([O:21][C@H:22]2[O:27][C@H:26]([CH2:28][OH:29])[C@@H:25]([OH:30])[C@H:24]([NH2:31])[C@H:23]2[OH:32])[C@@H:2]1[NH2:33]

Komponenten

8

Edukt 4

HCID 240BenzaldehydeHCID 313Hydrochloric Acid2×HCID 441374Kanamycin A SulfateHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 11274101(2S,3R,4R,5S,6S)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 21584188Chloroform methanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Kanamycin A sulphate (24.3 g., 0.03 mole) was dissolved in water (150 ml.) and the pH adjusted to 6 by the dropwise addition of 5 N hydrochloric acid. Sodium cyanoborohydride (1.95 g., 0.03 mole) was added and the mixture was cooled to 0° C. and stirred while a solution of benzaldehyde (3.61 g., 0.033 mole) dissolved in methanol (15 ml.) was added slowly over the course of 21/2 hours. The mixture was allowed to warm to room temperature. After 16 hours the pH of the solution was adjusted to 5.5 by the addition of 1 N hydrochloric acid and the solution was filtered and added to a column of Amberlite CG-50 ion-exchange resin in the ammonium-ion form. Elution first with water and then with a gradient of ammonium hydroxide of increasing concentration from 0-0.7 N gave as major product 3-N-benzylkanamycin A contaminated with some 1-N-benzyl derivative (5.0 g., 28%) Rf 0.44 in methanol-chloroform-17% ammonium hydroxide 4:1:2. (Kanamycin A gave an Rf value of 0.15).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. filtrationthe solution was filtered
  3. additionadded to a column of Amberlite CG-50 ion-exchange resin in the ammonium-ion form
  4. washElution first with water
  5. temperaturewith a gradient of ammonium hydroxide of increasing
  6. concentrationconcentration from 0-0.7 N
  7. customgave as major product

Quellen und Nachweise

ORD-Eintrag
ord-8e8dc00b65844fcb9bce73ad0bd98b12
Quelldatensatz
uspto-grants-1980_07
Patentnummer
US04214074

Verknüpfte Notizen

Wird geladen…