Dichloromethane → 2,3,4,6-Tetra-O-benzyl-1-O-(1-amino-hex-6-yl)-mannopyranose

HRID 1072284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1072284
[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.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:48]Cl.[NH:50]1[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51]1>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCOCC)C>[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][CH2:48][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][NH2:50])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 8082PiperidineHCID 10796Cesium carbonateHCID 110169932,3,4,6-Tetra-O-benzyl-D-mannopyranose

Produkt 1

HCID 697131992,3,4,6-Tetra-O-benzyl-1-O-(1-amino-hex-6-yl)-mannopyranose

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 10024DiethoxymethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture that consists of 54.1 g (100 mmol) of 2,3,4,6-tetra-O-benzyl-mannopyranose, 1.39 g (5 mmol) of tetrabutylammonium chloride and 35.84 g (110 mmol) of cesium carbonate in 500 ml of diethoxymethane is cooled to 0° C. At 0° C., 60.3 g (150 mmol) of 6-bromohexylamine-N-(9-fluorenylmethoxy-carbonyl) is added in drops over 30 minutes while being stirred vigorously. It is stirred for one hour at 0° C. 300 ml of dichloromethane is added, the organic phase is separated, and the aqueous phase is extracted twice with 200 ml of dichloromethane. The solvent of the combined organic phases is distilled off in a vacuum. The residue is taken up in 250 ml of ethanol, and 100 g (1.17 mol) of piperidine is added. It is stirred for five hours at 40° C. The solution is evaporated to the dry state, and the residue is chromatographed on silica gel (mobile solvent: dichloromethane/ethanol/triethylamine=20:2:0.1).

Aufarbeitung

  1. stirringIt is stirred for one hour at 0° C
  2. customthe organic phase is separated
  3. extractionthe aqueous phase is extracted twice with 200 ml of dichloromethane
  4. distillationThe solvent of the combined organic phases is distilled off in a vacuum
  5. stirringIt is stirred for five hours at 40° C
  6. customThe solution is evaporated to the dry state
  7. customthe residue is chromatographed on silica gel (mobile solvent: dichloromethane/ethanol/triethylamine=20:2:0.1)

Quellen und Nachweise

ORD-Eintrag
ord-6a29f3ba78ad4867b5a0c26dca2b3c09
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06908989B2

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