Methyl 1-C-[3-(benzo[b]thien-2-ylmethyl)-4-fluorophenyl]-α-D-glucopyranoside

A solution of 0.9M n-butyl magnesium chloride in tetrahydrofuran (0.9M, 7.3mL) was added to toluene (18.0mL) at -16 ° C and a solution of n-butyl lithium in n-hexane was added dropwise at -12~-16 ° C (2.66 M, 4.9 mL) and stirred at -12 to -15 ° C for 16 minutes.2- (5-bromo-2-fluorobenzyl) -1-benzothiophene (Compound I, 2.000 g) at -12 to -15 ° C, Of a toluene solution (10.0 mL)The reaction solution was dropped, At -12 to -16 ° CStir for one hour.A solution of 2, 3, 4, 6-di-O- (trimethylsilyl) -D-glucono-1, 5-lactone (Compound II, 3.197g) in toluene (10.0 ML) was added dropwise to the reaction solution, and the mixture was stirred at -12 to -15 ° C for 3 hours.The reaction mixture was poured into a methanol solution (10.0 mL) of methanesulfonic acid (3.0 mL) at 0 ° C or less, and the mixture was stirred at room temperature for 16 hours and 36 minutes. The reaction mixture was quenched by the addition of an aqueous sodium carbonate solution at a pH of about 8.The organic layer was washed with saturated brine (10 mL, once) and dried over anhydrous sodium sulfate, and extracted with ethyl acetate (50 mL, twice). After filtration, the filtrate was distilled off under reduced pressure, and the title compound (2.336 g, yield 86.4percent) was isolated from the obtained residue by silica gel column chromatography.

Molecular Weight:434.5
XLogP3:2.3
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:5
Exact Mass:434.11993778
Monoisotopic Mass:434.11993778
Topological Polar Surface Area:128
Heavy Atom Count:30
Complexity:584
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes