Thiazole (-zin) alkane ketone ring conjoined disaccharide compound, its preparation method and application in pharmaceutical preparation
A technology of compounds and alkanones, which is applied in the field of disaccharide compounds linked by thiazolidinone rings and its preparation, can solve problems such as the uncertainty of immune regulatory targets, the design of new immunomodulators and the difficulty in discovering structure-activity relationships, etc.
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Embodiment 1
[0064] Synthesis of (S)-3-(((2R,3S,4S,5R,6S)-tetrahydro-3,4,5-triacetyl-6-methoxy-2H-pyran-2-yl)methan Group)-2-((2R,3S,4R,5R)-tetrahydro-3,4-diacetyl-5-methoxyfuran-2-yl)thiazolidine-4-one (abbreviated as compound 3a) and (R)-3-(((2R,3S,4S,5R,6S)-tetrahydro-3,4,5-triacetyl-6-methoxy-2H-pyran-2-yl)methyl )-2-((2R,3S,4R,5R)-tetrahydro-3,4-diacetyl-5-methoxyfuran-2-yl)thiazolidine-4-one (abbreviated as compound 4a).
[0065] The chemical reaction is as follows:
[0066]
[0067] The specific method is:
[0068] (a) Weigh 150 mg (0.43 mmol) of azido sugar 1a (2,3,4-O-triacetyl-6-azidoglucose α-methylpyranoside) and sugar aldehyde 2b (2S, 3S) ,4R,5R)-tetrahydro-3,4-diacetyl-5-methoxyfuran-2-aldehyde) (1.0equiv) and dissolved in 3mL of anhydrous toluene, add triphenylphosphine (1.1equiv) , Stir for 60 minutes under nitrogen protection at room temperature;
[0069] (b) Add thioglycolic acid (2.0equiv), continue stirring at room temperature for 30 minutes, add anhydrous potassium carbona...
Embodiment 2
[0099] Synthesis of (S)-2-((2R,3S,4S,5R,6S)-tetrahydro-3,4,5-triacetyl-6-methoxy-2H-pyran-2-yl)methyl )-3-(((2R,3S,4R,5R)-tetrahydro-3,4-diacetyl-5-methoxyfuran-2-yl)thiazolidine-4-one (abbreviated as compound 3b) and (R)-2-((2R,3S,4S,5R,6S)-tetrahydro-3,4,5-triacetyl-6-methoxy-2H-pyran-2-yl)methyl) -3-(((2R,3S,4R,5R)-tetrahydro-3,4-diacetyl-5-methoxyfuran-2-yl)thiazolidine-4-one (abbreviated as compound 4b):
[0100] The chemical reaction process is as follows:
[0101]
[0102] The specific method is:
[0103] (a) Weigh 150mg (0.55mmol) of azido sugar 1b and aldehyde 2a (1.0equiv) and dissolve them in 3mL of dry toluene, add triphenylphosphine (1.1equiv), and stir for 60 minutes under nitrogen protection at room temperature;
[0104] (b) Add thioglycolic acid (2.0equiv), continue to stir at room temperature for 30 minutes, add anhydrous potassium carbonate powder to neutralize the reaction solution to pH=7, add dichloromethane (3×10mL) for extraction, combine the organic phases, a...
Embodiment 3
[0133] Synthesis of the disaccharide (S)-3-(((2R,3S,4S,5R,6S)-tetrahydro-3,4,5-trihydroxy-6-methoxy-2H-pyridine (Pyran-2-yl)methyl)-2-((2R,3S,4R,5R)-tetrahydro-3,4-dihydroxy-5-methoxyfuran-2-yl)thiazolidine-4-one (Hereinafter referred to as compound 5a)
[0134] The chemical reaction process is as follows:
[0135]
[0136] Weigh 0.16mmol of compound 3a prepared in Example 1 into a 25ml round-bottomed flask, add 5ml of anhydrous methanol to dissolve it, add (0.5equiv) sodium methoxide, and stir for 30 minutes under nitrogen protection at room temperature. TLC monitors the reaction, and the raw material disappears. Then, add 5 mL of methanol to dilute the solution, add cation exchange resin (Dowex-50) to neutralize to pH=7, filter, dry silica gel column chromatography (ethyl acetate: methanol 10:1) to obtain compound 5a.
[0137] According to the method described in Example 3, the following compounds with different optical isomers can also be obtained:
[0138] (R)-3-(((2R,3S,4S,5R,6...
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