Methanol → HCID 53688273, compound

HRID 2372159Notes

Reaction equation

HRID 2372159 reaction equation
C([O:4][C@H:5]1[C@@H:10]([CH2:11][O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:9][C@H:8]([O:20][CH2:21][C@H:22]2[O:29][C@H:26]([O:27][CH3:28])[C@H:25]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:24]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C@@H:23]2[O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C@H:7]([O:54][CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C@H:6]1[O:62][CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)(=O)C.CO.C[O-].[Na+]>C1(C)C=CC=CC=1>[CH2:31]([O:30][C@@H:25]1[C@@H:24]([O:38][CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C@H:23]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C@@H:22]([CH2:21][O:20][C@H:8]2[O:9][C@H:10]([CH2:11][O:12][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C@H:5]([OH:4])[C@H:6]([O:62][CH2:63][C:64]3[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=3)[C@H:7]2[O:54][CH2:55][C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=2)[O:29][C@@H:26]1[O:27][CH3:28])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 53849711Methyl 6-O-(4-O-acetyl-2,3,6-tri-O-benzyl-alpha-D-galactopyranosyl)-2,3,4-tri-O-benzyl-alpha-D-glucopyranoside

Product 1

HCID 53688273HCID 53688273, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 6-O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-galactopyranosyl)-2,3,4-tri-O-benzyl -α-D-glucopyranoside (2.314 g, 2.46 mmol) was dissolved in hot toluene (20 mL) and methanol (80 mL) was added, followed by a few drops of 1M. methanolic sodium methoxide. The mixture was stirred at room temperature during 2 h. The reaction mixture was made neutral with Amberlite IR 120 (H+) resin, filtered and concentrated under reduced pressure to afford methyl 2,3,4-tri-O-benzyl-6-O-(2,3,6-tri-O-benzyl-α-D-galactopyranosyl) -α-D-glucopyranoside (2.21 g, 100%) as an amorphous solid.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c157f87529b84f9eac8d59e326b6be76
Source dataset
uspto-grants-1992_03
Patent number
US05097023

Reaction notes

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