Synthesis of C-Glucosides from Grignard Reagents Prepared by Activated Magnesium

l-α-biaomo-2,3,4,6-tetra-O-acetyl-D-giucopyranose reacts with Grignard eagents prepared frorn the acnvated magnesium under very mild condition to ellord C- glucosides in a very high yield compared with Grignard Reagent prepared from usual method.β-anomer predominates in the reaction, mixture The configuration of anomers was assigned by 13C NMR spectra.

A new flavone C-glucoside from Glycosmis arborea(Rutaceae)

A new C-glycosyl flavone 7,4＇-dihydroxy-5-methoxyflavone-6-C-β-D-glucopyranoside 1 has been isolated and characterized form ethanolic extract of leaves part of Glycosmis arborea.The structure of compound was verified by means of high field 1D and 2D NMR（DEFT,COSY,DQF-HSQC,HMBC） and HRMS spectral analysis,respectively.

Design,synthesis and biological activity of cyclohexane-bearing C-glucoside derivatives as SGLT2 inhibitors

Seven cyclohexane-bearing C-glucoside derivatives（7,9,12,13 and 17-19） were designed and synthesized as SGLT2 inhibitors starting from a potent SGLT2 inhibitor we discovered in earlier work, （lS）-1-deoxy-l-[4-methoxy-3-（trans-n-propylcyclohexyl）methylphenyl]-D-glucose（1）.The in vitro and in vivo biological activities were evaluated by hSGLT2/hSGLTl inhibition and urinary glucose excretion （UGE）,respectively.Among the synthesized compounds 12,the 6-deoxy derivative of 1 was the most active and selective SGLT2 inhibitor（IC_（50）= 1.4nmol/L against hSGLT2;selectivity = 1576）.Compound 12 was a potent SGLT2 inhibitor,which could induce more urinary glucose than 1 and dapagliflozin in UGE.

Design,synthesis and in vivo anti-hyperglycemic activity of gem-dimethyl-bearing C-glucosides as SGLT2 inhibitors

A series of gem-dimethyl-bearing C-glucosides were designed and synthesized as SGLT2 inhibitors,with anhydrous aluminum chloride-mediated Friedel-Crafts alkylation to construct the gem-dimethyl functionality being the key step.The in vivo anti-hyperglycemic activity was evaluated with mice oral glucose tolerance test（OGTT）,and all the synthesized compounds showed significant but less potent anti-hyperglycemic activity than the positive control dapagliflozin.

Synthesis and Crystal Structure of 2,3,4,6-tetra-O-Acetyl-1-{4-chloro-3-[1-(4-ethoxyphenyl)-1-methylethyl]phenyl}-1-deoxy-β-D-glucopyranose

The title compound was synthesized and its crystal structure was determined by single-crystal X-ray diffraction.The crystal is of monoclinic system（C31H37ClO10,Mr = 605.06）,space group P21 with a = 11.882（5）,b = 10.106（5）,c = 13.816（6）,V = 1545.9（12）（A°）^3,Z = 2,Dc = 1.300 g/cm^3,F（000） = 640,μ = 0.179 mm^-1,the final R = 0.0430 and wR = 0.0595 for 4960 observed reflections（I 〉 2σ（I））.The title compound was confirmed to be a β-anomer by single-crystal X-ray diffraction and 1H NMR.The proximal benzene ring is nearly orthogonal to the glucopyranoside ring,and the two benzene rings are also almost orthogonal to each other.Four non-classical intermolecular hydrogen bonds observed in the crystal lattice help to stabilize the crystal.