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 971459

반응식

HRID 971459 반응식
[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]

참가 물질

8

반응물 4

HCID 240BenzaldehydeHCID 313Hydrochloric Acid2회HCID 441374Kanamycin A SulfateHCID 5003444Sodium cyanoborohydride

생성물 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

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 21584188Chloroform methanol용매

반응 조건

온도
0 °C

실험 절차

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 5N 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 2 1/2 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 1N 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 0-0.7N 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).

후처리

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

출처 및 근거

ORD 기록
ord-2653f3c8e3a6495dbeca559964c45727
출처 데이터셋
uspto-grants-1979_07
특허 번호
US04160082

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