N-bromobutanimide → 2,3,4,6-Tetra-O-benzyl-alpha-D-galactopyranosyl Fluoride

Participants

Role	Name	HCID	Charge
Reactant	N-bromobutanimide	HCID 67184	—
Reactant	(Diethylamino)sulfur trifluoride	HCID 123472	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	(2R,3S,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-(phenylthio)tetrahydro-2H-pyran	HCID 11104159	—
Solvent	Dichloromethane	HCID 6344	—
Product	2,3,4,6-Tetra-O-benzyl-alpha-D-galactopyranosyl Fluoride	HCID 9959029	73.4%

Reaction Conditions

Temperature	-15 °C

Reaction Steps

To a solution of 10 (10.0 g, 15.82 mmol, 1 eq) in dry CH2Cl2 (191 mL) under argon at −15° C. were added diethylaminosulfur trifluoride (3.14 mL, 23.73 mmol, 1.5 eq) and, after 2 min, N-bromosuccinimide (3.66 g, 20.57 mmol, 1.3 eq). After being stirred at −15° C. for 30 min the reaction was diluted with CH2Cl2 (420 mL) and poured into a cold saturated aqueous NaHCO3 solution (195 mL). The organic layer was dried over MgSO4 and concentrated. Purification by flash chromatography on silica gel (petroleum ether/EtOAc 94:6) afforded 11 as viscous syrup (6.3 g, 73%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08211859B2
Source dataset	uspto-grants-2012_07
ORD ID	ord-1c29419f07504d2ab5eb1c6bfcd3f456
Source note	uspto-grants-2012_07