4-Methoxyphenyl-3-O-allyl-2,4,6-tri-O-benzyl-b-D-galactopyranoside → 4-Methoxyphenyl 2,4,6-tri-O-benzyl-beta-D-galactopyranoside

HRID 1067047Notes

Reaction equation

HRID 1067047 reaction equation
C([O:4][C@H:5]1[C@@H:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@@H:18]([CH2:28][O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:17][C@@H:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[C@@H:6]1[O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)C=C>CO.C1(C)C=CC=CC=1.Cl[Pd]Cl>[CH2:38]([O:37][C@@H:6]1[C@@H:5]([OH:4])[C@@H:19]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@@H:18]([CH2:28][O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[O:17][C@H:7]1[O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

5

Reactant 1

HCID 105794064-Methoxyphenyl-3-O-allyl-2,4,6-tri-O-benzyl-b-D-galactopyranoside

Product 1

HCID 107691424-Methoxyphenyl 2,4,6-tri-O-benzyl-beta-D-galactopyranosideYield 94%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Compound 9 (2.67 g, 4.49 mmol) was dissolved in a mixture of anhydrous methanol and toluene (21 mL, v/v 3:1) and reacted with PdCl2 (˜100 mg) under nitrogen and at room temperature. After 4 hours of reaction, the reaction mixture was filtrated over a pad of Celite and the solvents were evaporated. Purification of the residue by chromatography on silica gel (ethyl acetate-petroleum ether, v/v 1:4) afforded 10 as white crystals in 94% yield (2.35 g). mp=84-86° C.; [αD]24 =−11° (c 1, CHCl3); 1H NMR (500 MHz, CDCl3): δ3.66-3.73 (m, 3H, H-5, H-6a and H-6b), 3.74 (t, 1H, J2,3 9.5 Hz, J3,4 2.9 Hz, H-3), 3.76 (s, 3H, OMe), 3.83 (dd, 1H, J1,2 7.7 Hz, H-2), 3.90 (d, 1H, J4,5<1.5 Hz, H-4), 4.44, 4.49, 4.66, 4.78, 4.81 and 5.05 (6 d, 1H each, JA,B 11.8 Hz, CH2Ph), 4.84 (d, 1H, H-1), 6.78 and 7.02 (2 d, 2H each, C6H4), 7.22-7.40 (m, 15H, 3C6H5). Anal. Calcd for C34H36O7 (556.7): C 73.36, H 6.52; found: C 72.96, H 6.63.

Workup

  1. customAfter 4 hours of reaction
  2. filtrationthe reaction mixture was filtrated over a pad of Celite
  3. customthe solvents were evaporated
  4. customPurification of the residue by chromatography on silica gel (ethyl acetate-petroleum ether, v/v 1:4)

Sources & evidence

ORD record
ord-d751ce395f054972bf81545c1231bacb
Source dataset
uspto-grants-2001_06
Patent number
US06245902B1

Reaction notes

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