HCID 11549452, compound → 2-(Trimethylsilyl)ethyl lactoside
Reaction equation
C([O:4][C@@H:5]1[C@@H:17]([O:18]C(=O)C)[C@H:16]([O:22][C@@H:23]2[O:40][C@H:39]([CH2:41][O:42]C(=O)C)[C@H:34]([O:35]C(=O)C)[C@H:29]([O:30]C(=O)C)[C@H:24]2[O:25]C(=O)C)[C@@H:15]([CH2:46][O:47]C(=O)C)[O:14][C@H:6]1[O:7][CH2:8][CH2:9][Si:10]([CH3:13])([CH3:12])[CH3:11])(=O)C>C[O-].[Na+]>[C@@H:23]1([O:22][C@@H:16]2[C@@H:15]([CH2:46][OH:47])[O:14][C@@H:6]([O:7][CH2:8][CH2:9][Si:10]([CH3:13])([CH3:12])[CH3:11])[C@H:5]([OH:4])[C@H:17]2[OH:18])[O:40][C@H:39]([CH2:41][OH:42])[C@H:34]([OH:35])[C@H:29]([OH:30])[C@H:24]1[OH:25]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Trimethylsilylethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (1) (Jansson et al., 1988) (29.4 g, 40 mmol) was stirred in methanolic sodium methoxide (5.8 mM, 515 mL) for 15 h. Neutralization with acetic acid, evaporation and crystallization from ethanol gave (2) (14.6 g, 82%).
Workup
- custom