Potassium Hydroxide → 2,3,4,6-Tetra-O-benzyl-1-O-(1-amino-prop-3-yl)-galactopyranose

HRID 1072283

반응식

HRID 1072283 반응식
[CH2:1]([O:8][C@@H:9]1[C@@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:13]([CH2:32][O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:12][CH:10]1[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Br[CH2:44][CH2:45][CH2:46][N:47]1C(=O)C2=CC=CC=C2C1=O.O.NN>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCOCC)C.COCCOC.C1C=CC=CC=1>[CH2:1]([O:8][C@@H:9]1[C@@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:14]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C@@H:13]([CH2:32][O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[O:12][CH:10]1[O:11][CH2:44][CH2:45][CH2:46][NH2:47])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

9

반응물 4

HCID 14797Potassium HydroxideHCID 21611N-3-BromopropylphthalimideHCID 24654Hydrazine hydrate (1:1)HCID 27341542,3,4,6-Tetrakis-O-(phenylmethyl)-D-galactopyranose

생성물 1

HCID 697151682,3,4,6-Tetra-O-benzyl-1-O-(1-amino-prop-3-yl)-galactopyranose

시약·촉매·용매 4

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 241Benzene용매HCID 80711,2-Dimethoxyethane용매HCID 10024Diethoxymethane용매

반응 조건

온도
10 °C

실험 절차

A mixture that consists of 42.1 g (100 mmol) of 2,3,4,6-tetra-O-benzyl-galactopyranose, 1.7 g (5 mmol) of tetrabutylammonium hydrogen sulfate and 33.7 g (600 mmol) of fine-powder potassium hydroxide in 350 ml of diethoxymethane is cooled to 10° C. At 10° C., 40.2 g (150 mmol) of N-(3-bromopropyl)-phthalimide, dissolved in 100 ml of 1,2-dimethoxyethane, is added in drops over 40 minutes while being stirred vigorously. It is stirred for three hours at 10° C. 300 ml of benzene is added, solid is filtered out, and the filtrate is evaporated to the dry state in a vacuum. The filtrate residue is dissolved in 500 ml of ethanol, 25.03 ml of hydrazine hydrate (500 mmol) is added, and it is refluxed for six hours. It is allowed to cool to 0° C., deposited precipitate is filtered out, and the filtrate is evaporated to the dry state in a vacuum. The residue is dissolved in 400 ml of dichloromethane, this solution is washed twice with 5% aqueous sodium hydroxide solution, then once with water (in each case 300 ml). The organic phase is evaporated to the dry state in a vacuum, and the residue is chromatographed on silica gel (mobile solvent: dichloromethane/ethanol/triethylamine=20:2:0.1).

후처리

  1. additionis added in drops over 40 minutes
  2. stirringIt is stirred for three hours at 10° C
  3. filtrationsolid is filtered out
  4. customthe filtrate is evaporated to the dry state in a vacuum
  5. dissolutionThe filtrate residue is dissolved in 500 ml of ethanol
  6. temperatureit is refluxed for six hours
  7. temperatureto cool to 0° C.
  8. filtrationis filtered out
  9. customthe filtrate is evaporated to the dry state in a vacuum
  10. dissolutionThe residue is dissolved in 400 ml of dichloromethane
  11. washthis solution is washed twice with 5% aqueous sodium hydroxide solution
  12. customThe organic phase is evaporated to the dry state in a vacuum
  13. customthe residue is chromatographed on silica gel (mobile solvent: dichloromethane/ethanol/triethylamine=20:2:0.1)

출처 및 근거

ORD 기록
ord-c046074a441547b880b05a76c6fc7921
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06908989B2

연결된 노트

불러오는 중…