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

HRID 1636191Notes

Reaction equation

HRID 1636191 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)-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

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

Sources & evidence

ORD record
ord-8221e5032d994b9587fbd0e6536d3458
Source dataset
uspto-grants-2000_03
Patent number
US06033669

Reaction notes

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