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

反応式

HRID 971459 の反応式
[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]

参加物

8

反応物 4

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

生成物 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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 21584188Chloroform methanol溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2653f3c8e3a6495dbeca559964c45727
出典データセット
uspto-grants-1979_07
特許番号
US04160082

関連ノート

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