Method for synthesizing alpha-linked disaccharide by randomly glycosylating unprotected monosaccharide
An unprotected, chemical synthesis technology, applied in chemical instruments and methods, organic chemistry, sugar derivatives, etc., can solve problems such as expensive, time-consuming and labor-intensive the effect
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Embodiment 1
[0029] Synthesis of α-Linked Disaccharides from Compound 1 and Compound 2
[0030]
[0031] Compound 1 (300mg, 0.65mmol) and compound 2 (1.3mmol) were dissolved in anhydrous dioxane (5mL), then calcium sulfate (500mg) was added, and after nitrogen protection, the reaction mixture was stirred at room temperature for 30min; Add boron trifluoride diethyl ether (29mg, 0.13mmol) and continue to stir the reaction for 14h; then add triethylamine (0.1mL) to stop the reaction; the reacted mixture is filtered through celite to remove solids, washed with dioxane; evaporated After removing the solvent, the residue was purified by silica gel column chromatography, and the eluent was a mixture of dichloromethane:methanol with a volume ratio of 10:1; the purified product was dissolved in methanol (5mL), and Pd / C (100mg) was added, Stir the reaction with hydrogen at room temperature for 48 hours; filter and collect the filtrate, evaporate the solvent, and purify the residue by C-18 column ...
Embodiment 2
[0033] Synthesis of α-Linked Disaccharides from Compound 1 and Compound 3
[0034]
[0035] Compound 1 (300mg, 0.65mmol) and compound 2 (1.3mmol) were dissolved in anhydrous dioxane (5mL), then calcium sulfate (500mg) was added, and after nitrogen protection, the reaction mixture was stirred at room temperature for 30min; Add boron trifluoride diethyl ether (29mg, 0.13mmol) and continue to stir the reaction for 14h; then add triethylamine (0.1mL) to stop the reaction; the reacted mixture is filtered through celite to remove solids, washed with dioxane; evaporated After removing the solvent, the residue was purified by silica gel column chromatography, and the eluent was a mixture of dichloromethane:methanol with a volume ratio of 10:1; the purified product was dissolved in methanol (5mL), and Pd / C (100mg) was added, Stir the reaction with hydrogen at room temperature for 48 hours; filter and collect the filtrate, evaporate the solvent, and purify the residue by C-18 column ...
Embodiment 3
[0037] Synthesis of α-Linked Disaccharides from Compound 1 and Compound 4
[0038]
[0039] Compound 1 (300mg, 0.65mmol) and compound 2 (1.3mmol) were dissolved in anhydrous dioxane (5mL), then calcium sulfate (500mg) was added, and after nitrogen protection, the reaction mixture was stirred at room temperature for 30min; Add boron trifluoride diethyl ether (29mg, 0.13mmol) and continue to stir the reaction for 14h; then add triethylamine (0.1mL) to stop the reaction; the reacted mixture is filtered through celite to remove solids, washed with dioxane; evaporated After removing the solvent, the residue was purified by silica gel column chromatography, and the eluent was a mixture of dichloromethane:methanol with a volume ratio of 10:1; the purified product was dissolved in methanol (5mL), and Pd / C (100mg) was added, Stir the reaction with hydrogen at room temperature for 48 hours; filter and collect the filtrate, evaporate the solvent, and purify the residue by C-18 column ...
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