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

HRID 1072284ノート

反応式

HRID 1072284 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 70681Tetrabutylammonium Chloride触媒HCID 10024Diethoxymethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-6a29f3ba78ad4867b5a0c26dca2b3c09
出典データセット
uspto-grants-2005_06
特許番号
US06908989B2

反応ノート

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