Phenol → phenyl 2,3,5,6-tetra-O-propanoyl-beta-D-glucofuranoside

HRID 1167966Notes

Reaction equation

HRID 1167966 reaction equation
C(O[C@@H:6]1[O:20][C@H:19]([C@@H:21]([CH2:27][O:28][C:29](=[O:32])[CH2:30][CH3:31])[O:22][C:23](=[O:26])[CH2:24][CH3:25])[C@H:13]([O:14][C:15](=[O:18])[CH2:16][CH3:17])[C@H:7]1[O:8][C:9](=[O:12])[CH2:10][CH3:11])(=O)CC.[C:33]1([OH:39])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.B(F)(F)F.CCOCC>C(Cl)Cl>[C:9]([O:8][C@@H:7]1[C@@H:13]([O:14][C:15](=[O:18])[CH2:16][CH3:17])[C@@H:19]([C@@H:21]([CH2:27][O:28][C:29](=[O:32])[CH2:30][CH3:31])[O:22][C:23](=[O:26])[CH2:24][CH3:25])[O:20][C@H:6]1[O:39][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:12])[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 996PhenolHCID 8000Boron trifluoride etherateHCID 106238281,2,3,5,6-Penta-O-propanoyl-beta-D-glucofuranose

Product 1

HCID 70024167phenyl 2,3,5,6-tetra-O-propanoyl-beta-D-glucofuranosideYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,2,3,5,6-Penta-O-propanoyl-β-D-glucofuranose (1.0 g, 2.2 mmol) and phenol (0.41 g, 4.3 mmol) were dissolved in CH2Cl2 (10 mL) and boron trifluoride diethyl etherate (134 μL, 1.1 mmol) was added dropwise. The solution was left at room temperature overnight by which time the reaction was complete by TLC. The reaction mixture was washed with saturated aqueous NaHCO3 (30 mL), water, dried (MgSO4) and concentrated in vacuo. Flash silica chromatography of the residue, eluting with 15% ethyl acetate in petroleum ether, gave phenyl 2,3,5,6-tetra-O-propanoyl-β-D-glucofuranoside as a colourless syrup (0.8 g, 77%); δH (CDCl3) 7.29 (2H, dd, J 7.4 and 8.4, 3′-and 5′-H), 7.02 (1H, t, J 7.4, 4′-H), 7.01 (2H, d, J 8.4, 2′- and 6′-H), 5.63 (1H, s, 1-H), 5.46 (1H, d, J 5.0, 3-H), 5.31 (1H, ddd, J 9.4, 4.6 and 2.4, 5-H), 5.27 (1H, s, 2-H), 4.62 (1H, dd, J 9.4 and 5.0, 4-H), 4.54 (1H, dd, J 12.3 and 2.4, 6a-H), 4.09 (1H, dd, J 12.3 and 4.6, 6b-H), 2.42 (2H, q, J 7.5, CH2), 2.39 (2H, q, J 7.5, CH2), 2.33 (2H, q, J 7.5, CH2), 2.25 (2H, q, J 7.5, CH2), 1.17 (3H, t, J 7.5, CH3), 1.15 (3H, t, J 7.5, CH3), 1.13 (3H, t, J 7.5, CH3), 1.08 (3H, t, J 7.5, CH3); δC (CDCl3) 174.3, 173.3, 173.3, 173.0 (4×C═O), 156.6 (1′-C), 130.0 (3′- and 5′-C), 122.9 (4′-C), 116.9 (2′- and 6′-C), 104.6 (1-C), 80.7 (2-C), 79.7 (4-C), 73.6 (3-C), 68.9 (5-C), 63.2 (6-C), 27.8, 27.8, 27.8, 27.7 (4×CH2), 9.4, 9.2, 9.2, 9.1 (4×CH3).

Workup

  1. washThe reaction mixture was washed with saturated aqueous NaHCO3 (30 mL), water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. washFlash silica chromatography of the residue, eluting with 15% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-8658e5186fbb43e6aebdb5aac7cfaaeb
Source dataset
uspto-grants-2003_09
Patent number
US06620921B1

Reaction notes

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