Thiophenol → Phenyl 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-galactopyranoside

HRID 1637427

反応式

HRID 1637427 の反応式
[C:1]([O:4][C@H:5]([C@H:8]([C@H:13]([C@@H:18]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:19][C:20](=[O:22])[CH3:21])[O:14][C:15](=[O:17])[CH3:16])[O:9][C:10](=O)C)C=O)(=[O:3])[CH3:2].[C:28]1([SH:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl>[C:28]1([S:34][C@@H:10]2[O:9][C@H:8]([CH2:5][O:4][C:1](=[O:3])[CH3:2])[C@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:23]2[O:24][C:25](=[O:27])[CH3:26])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

参加物

4

反応物 2

HCID 7969ThiophenolHCID 81232D-galactose, 2,3,4,5,6-pentaacetate

生成物 1

HCID 10950254Phenyl 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-galactopyranoside収率 96%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of galactose pentaacetate (5.00 g, 12.8 mmol) in 125 mL of CH2Cl2 is added thiophenol (1.49 mL, 14.1 mmol) and boron trifluoride diethyl ether complex (4.73 mL, 38.4 mmol). The reaction mixture is stirred at room temperature for 5 h and then poured into 200 mL of ice water. The organic layer is washed with saturated NaHCO3 (200 ml), dried over Na2SO4, filtered, concentrated and purified by flash chromatography (35% EtOAc/hexane) to give 5.4 g (96%) of 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 39: Rf 0.22 (35% EtOAc/hexane); 1H NMR (CDCl3, 270 MHz) δ 7.35-7.65 (m, 5 H, ArH), 5.50 (br d, J=3.3 Hz, 1 H, H-4), 5.32 (t, J=9.8 Hz, 1 H, H-2), 5.13 (dd, J=9.8, 3.3 Hz, 1 H, H-3), 4.80 (d, J=9.8 Hz, 1 H, H-1), 4.13-4.32 (m, 2 H, H-6, H-6'), 4.02 (br t, J=6.5 Hz, 1 H, H-5), 2.02-2.23 (4s, 12 H, OAc).

後処理

  1. washThe organic layer is washed with saturated NaHCO3 (200 ml)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography (35% EtOAc/hexane)

出典と根拠

ORDレコード
ord-13e06809a7c340b4bd1d74d850fe752d
出典データセット
uspto-grants-2000_03
特許番号
US06040433

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