HCID 11549452, compound → 2-(Trimethylsilyl)ethyl 4-O-hexopyranosylhexopyranoside

HRID 2393228Notes

Reaction equation

HRID 2393228 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

HCID 11549452HCID 11549452, compound

Product 1

HCID 1951692-(Trimethylsilyl)ethyl 4-O-hexopyranosylhexopyranosideYield 82.5%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

2-Trimethylsilylethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-B-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

  1. customNeutralization with acetic acid, evaporation and crystallization from ethanol

Sources & evidence

ORD record
ord-e6e76f1d39a049988d713c0c75d862a4
Source dataset
uspto-grants-1998_09
Patent number
US05807559

Reaction notes

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