Water → 4-O-benzyl-3,6-di-O-acetyl-D-glucose

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	[(2R,3S,4R)-4-acetyloxy-3-phenylmethoxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate	HCID 2734732	—
Reactant	Hydrobromide monohydrate	HCID 22326455	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	4-O-benzyl-3,6-di-O-acetyl-D-glucose	HCID 86654839	—

Reaction Steps

48% Hydrobromic acid water solution (0.5 mL) was added to a mixture of 4-O-benzyl-3,6-di-O-acetyl-D-glucal (5 mmol) in tetrahydrofuran (50 mL), and obtained solution was stirred in room temperature. After reaction was completed (TLC) the reaction mixture was poured into the 10% water solution of sodium bicarbonate (125 mL), and water solution was extracted with ethyl acetate (3×30 mL). Combined organic extracts were washed with water and dried over sodium sulfate. Drying agent and solvents were removed and product was purified by column chromatography (SilicaGel 60 Merck), using hexanes:ethyl acetate as eluents.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08927506B2
Source dataset	uspto-grants-2015_01
ORD ID	ord-263635c797c5441f9a11b6f5bc0ab991
Source note	uspto-grants-2015_01