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

HRID 1637427

Reaction equation

HRID 1637427 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-13e06809a7c340b4bd1d74d850fe752d
Source dataset
uspto-grants-2000_03
Patent number
US06040433

Linked notes

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