Sugar acid compound and use thereof
A compound and acid technology, applied in the field of sugar-acid compounds, can solve the problems of low lipophilic coefficient and poor membrane permeability, and achieve the effect of good anti-tumor activity, high efficiency and low toxicity and anti-diabetes
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[0023] Said preparation method comprises the steps:
[0024] A, the compound shown in formula (A) [abbreviated as compound (A), and so on, hereinafter with the same abbreviation method to represent the compound], the preparation of compound (A) is referring to the literature Tetrahedron Letters.2005, 46, 7081-7085. and Carbohydrate.Research, 343, (2008) 773-779 method synthesis, dissolved in an appropriate amount of dry CH 3 OH, drop a catalytic amount of 0.1N CH 3 ONa / CH 3 OH solution, thin-layer chromatography (TLC) tracking detection, when the initial substance disappears, add an appropriate amount of H + Type cation exchange resin, stirred for 10 minutes, filtered, and the filtrate was decompressed to remove the solvent to obtain compound (A-1);
[0025] B, compound (B-1) (commercially available: produced by Lancaster) and compound (A-1) were dissolved in an appropriate amount of dry pyridine respectively (that is, placed in two mutually independent reactors, the same b...
Embodiment 1
[0035] (1) Synthesis of 2-(β-D-glucopyranosyl)-1,4-dimethoxybenzene
[0036]
[0037] The crude compound 2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-dimethoxybenzene (1.27 g, 2.71 mmol) was dissolved in 5 mL Dry MeOH, add a catalytic amount of 0.1N MeONa / MeOH solution dropwise, stir for 35 minutes, TLC detection shows that the initial substance disappears, add an appropriate amount of H + Type cation exchange resin [Shanghai Lvbao cation exchange resin model: 001*7 (732)], stirred for 10 min, filtered, and the filtrate was decompressed to remove the solvent to obtain a white solid 2-(β-D-glucopyranosyl)-1, 4-Dimethoxybenzene (678.2 mg, 83.2%, R f4 =0.42, CH 2 Cl 2 : MeOH=6:1), directly used in the next reaction.
[0038] (2) 2-(2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranose)-1,4-dimethoxy Benzene synthesis
[0039]
[0040] The compound 2-(β-D-glucopyranosyl)-1,4-dimethoxybenzene (118.2 mg, 0.39 mmol) was dissolved in 2 mL of dry pyridine, ...
Embodiment 2
[0060] (1) Synthesis of 2-(β-D-glucopyranosyl)-1,4-dimethoxynaphthalene
[0061]
[0062] The compound 2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranose)-1,4-dimethoxynaphthalene (91.5 mg, 0.18 mmol) was dissolved in anhydrous methanol (5mL), add the newly prepared 0.1N MeONa / MeOH solution of catalytic amount, stir 35min, TLC shows that initial matter disappears, adds H + Type cation exchange resin [Shanghai Lvbao cation exchange resin model: 001*7 (732)] was stirred for 15 minutes, filtered, concentrated, and separated by column chromatography (EtOAc→EtOAc:EtOH=5:1→2:1→EtOH), without Water Et 2 O recrystallized to give white powder 2-(β-D-glucopyranosyl)-1,4-dimethoxynaphthalene synthesis (60.1mg, 97.2%): R f =0.40 (EtOAc:MeOH=8:1); mp80-83°C (EtOAc 2 O); [α] D 22.6 =+2.3 (c=0.54, MeOH); IR (KBr, cm -1 )3404(-OH);
[0063] 1 H NMR (500.13MHz, D 2 O): δ 8.20, 8.07 (2d, 2H, J=8.3Hz, H-5, H-8, ArH), 7.60 (m, 2H, H-6, H-7, ArH), 6.96 (s, 1H , H-3, ArH), 4.87 (d, 1H, J 1’，...
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