Glycoside derivatives and uses thereof
a technology of glycoside and derivatives, applied in the field of glycoside derivatives, can solve the problems of severe long-term complications, damage to blood vessels, severe vision loss or blindness, etc., and achieve the effects of prophylactic treatment, management, treatment, and adjunct treatmen
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Example 1
Synthesis of (R)-2-Amino-3-methyl-butyric Acid (2R,3S,4R,5R,6S)-6-[3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-4-ethyl-phenyl]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl Ester
[0295]
[0296]STEP I: To a stirred solution of (2S,3R,4R,5S,6R)-2-[3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-4-ethyl-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (Intermediate 2, 6.0 g, 14.40 mmol) in pyridine (60 ml) was added trityl chloride (4.8 g, 17.28 mmol) followed by DMAP (0.18 g, 1.44 mmol) at room temperature. Then the reaction mixture was heated at 80° C. After stirring for 16 h, pyridine was evaporated under reduced pressure. Resulting residue was taken in ethyl acetate (100 ml), washed with aq. copper sulfate solution (50 ml), brine (100 ml), dried over sodium sulfate, concentrated and purified by silica gel column chromatography to give 8.10 g of (2S,3R,4R,5S,6R)-2-[3-(2,3-dihydro-benzo[1,4]dioxi n-6-ylmethyl)-4-ethyl-phenyl]-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol as whi...
example 2
Synthesis of Carbonic Acid (2R,3S,4R,5R,6S)-6-[4-cyclopropyl-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl methyl)-phenyl]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl Ester Methyl Ester
[0308]
[0309]STEP I: To a stirred solution of (2S,3R,4R,5S,6R)-2-[4-Cyclopropyl-3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
[0310](Intermediate 3, 890 mg, 2.1 mmol) in collidine (7 ml) was added a solution of methyl chloroformate (0.21 ml, 2.5 mmol) in DCM (0.5 ml) at −40° C. After stirring for 1 h at same temperature, it was stirred at room temperature for 1.5 h. Reaction mixture was poured into ice cold 10% HCl solution and extracted with ethyl acetate (2×10 ml). Combined organic layers were washed with brine (10 ml), dried over sodium sulfate, concentrated and purified by silica gel column chromatography to give 1.1 g of carbonic acid (2 R, 3S,4 R, 5R, 6S)-6-[4-cyclopropyl-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl methyl)-phenyl]-3,4,5-trihydroxy-tetrahydro-pyr...
example 3
Synthesis of Phosphoric Acid (2R,3S,4R,5R,6S)-6-[3-(2,3-dihydro-benzo[1,4]dioxin-6-yl methyl)-4-ethyl -phenyl]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl Ester Diethyl Ester
[0313]
[0314]To a stirred solution of (2S,3R,4R,5S,6R)-2-[3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-4-ethyl-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (Intermediate 2, 500 mg, 1.2 mmol) in pyridine (5 ml) was added diethylchlorophosphate (0.27 ml, 1.9 mmol) at −40° C. After stirring for 1 h at same temperature, reaction was quenched with the addition of 1N HCl and extracted with ethyl acetate (2×10 ml). Combined organic layers were washed with brine (10 ml), dried over sodium sulfate, concentrated and purified by preparative HPLC to give 220 mg of phosphoric acid (2R,3S,4R,5R,6S)-6-[3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-4-ethyl-phenyl]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester diethyl ester as a white solid.
[0315]1H NMR (400 MHz, CD3OD): δ1.07 (t, J=7.6 Hz, 3H), 1.15 (td J=7.2, 1.2 Hz...
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