C-Arylglucoside synthesis: triisopropylsilane as a selective reagent for the reduction of an anomeric C-phenyl ketal

Discovery of Dapagliflozin: A Potent, Selective Renal Sodium-Dependent Glucose Cotransporter 2 (SGLT2) Inhibitor for the Treatment of Type 2 Diabetes

“…53 Reduction of the anomeric methoxy group of 12 using triethylsilane and BF 3 · OEt 2 , followed by peracetylation, yielded tetraacetate 13 in 55% for the two steps after recrystallization from ethanol to remove the small amount of the R-anomer formed during the reduction. 54 Hydrolysis of 13 with lithium hydroxide generated 6 in quantitative yield. …”

Recent Advances in Aryl C-Glycoside Synthesis

“…This was superior to other reducing reagents such as PhSiH 3 (2:1), Me 2 PhSiH (4:1), Ph 3 SiH (16:1), and DIBAL (25:1) (Scheme 11) [36].…”

C-Aryl glucoside SGLT2 inhibitors containing a biphenyl motif as potential anti-diabetic agents

“…Reaction of 15 with t-butyllithium, followed by addition of the nascent lithiated aromatic compounds to gluconolactone, produced lactols, which were converted in situ to the desilylated O-methyl lactols by treatment with methansulfonic acid in methanol at low temperatures (-78°C to -50°C). Reduction of the methoxy group of the lactols using triethylsilane and boron trifluoride diethyl etherate [19] generated the target compounds 16(a, b, c, d, e, f, g, h, i and j).…”