Sodium Methoxide → HCID 22806759, compound
Reaction equation
[C:1]([NH:4][C@@H:5]1[C@@H:23]([OH:24])[C@H:22]([O:25][C@@H:26]2[O:55][C@@H:54]([CH3:56])[C@@H:45]([O:46]CC3C=CC=CC=3)[C@@H:36]([O:37]CC3C=CC=CC=3)[C@@H:27]2[O:28]CC2C=CC=CC=2)[C@@H:21]([CH2:57][OH:58])[O:20][C@H:6]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])(=[O:3])[CH3:2].C[O-].[Na+]>CO>[C:1]([NH:4][C@@H:5]1[C@@H:23]([OH:24])[C@H:22]([O:25][C@@H:26]2[O:55][C@@H:54]([CH3:56])[C@@H:45]([OH:46])[C@@H:36]([OH:37])[C@@H:27]2[OH:28])[C@@H:21]([CH2:57][OH:58])[O:20][C@H:6]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])(=[O:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The syrupy product was used directly for the preparation of 8-methoxycarbonyloctyl 2-acetamido-4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside. The crude disaccharide (3.78 g) was dissolved in 50 ml of dry methanol, and 5 ml of 0.2 N sodium methoxide in methanol was added. After 24 h at room temperature, the solution was deionized using the acid resin. Solvent removal left an oil which was dissolved in dichloromethane (100 ml). The solution was washed with water and dried over magnesium sulfate prior to evaporation to a residue (1.01 g, 85% yield) from the fully blocked disaccharide. Purification was by recrystallization from ethyl acetate-hexane, mp 145°-146°, [α]D25 -33.6° (c 1.2, chloroform).
Workup
- customSolvent removal
- waitleft an oil which
- dissolutionwas dissolved in dichloromethane (100 ml)
- washThe solution was washed with water
- dry with materialdried over magnesium sulfate
Sources & evidence
- ORD record
- ord-a3b47a20292d4bf7bd5a089f21445a16
- Source dataset
- uspto-grants-1980_12
- Patent number
- US04238473
Reaction notes
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