Synthesis and evaluation of new 6-deoxy-6-fluorinated glucosides as inhibitors of yeast α-glucosidase

Delineating the physical organic profile of the 6-fluoro glycosyl donor

“…Attempts to hydrolyse the methyl acetal of 6 to the corresponding lactol (C1-OH) 8 proved difficult [18]. A two-step protocol was therefore implemented, beginning with the treatment of 6 with BCl 3 ÁSMe 2 in CH 2 Cl 2 for 30 min at ambient temperature [19]. This successfully generated the chloroacetal 7 exclusively as the a-anomer in 46% isolated yield, which was then exposed to a mixture of DMF and saturated aqueous NaHCO 3 to give the desired lactol 8 in 92% yield.…”