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tert-amyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
70%
With zinc dibromide; In chloroform; at 72℃; for 0.75h;Microwave irradiation;
General procedure: In a typical reaction (Scheme 1), anhydrous ZnBr2(0.5 mmol) was added to a mixture of 3,4,6- tri-O-acetyl glucal (5 mmol) and a phenol or alcohol (4.5 mmol) in CHCl3(8 mL). A Teflon heating button and a stirring bar were introduced into the flask, which was then equipped with condenser and irradiated with microwave radiation(400 W) under open-vessel conditions in a Milestone START-S microwave labstation at 72C for a specified time period (Tables 1-5). After the completion of the reaction, water (15 ml) was added to the reaction mixture and the organic layer was separated. The aqueous layer was extracted with chloroform (25 ml). The combined organic layers was dried over anhydrous Na2SO4 and concentrated to afforda syrupy crude mass, which was refined by column chromatography on silica gel(100-200 mesh) using ethyl acetate (5-10%) in petroleum ether (60-80 C) as the eluent.The ratio of alpha and beta anomers, which had close Rf values and eluted together, was determined by integration of the corresponding hydrogen signals in the 1HNMR of the crude product.
With zinc dibromide; In chloroform; at 72℃; for 0.916667h;Microwave irradiation;
General procedure: In a typical reaction (Scheme 1), anhydrous ZnBr2(0.5 mmol) was added to a mixture of 3,4,6- tri-O-acetyl glucal (5 mmol) and a phenol or alcohol (4.5 mmol) in CHCl3(8 mL). A Teflon heating button and a stirring bar were introduced into the flask, which was then equipped with condenser and irradiated with microwave radiation(400 W) under open-vessel conditions in a Milestone START-S microwave labstation at 72C for a specified time period (Tables 1-5). After the completion of the reaction, water (15 ml) was added to the reaction mixture and the organic layer was separated. The aqueous layer was extracted with chloroform (25 ml). The combined organic layers was dried over anhydrous Na2SO4 and concentrated to afforda syrupy crude mass, which was refined by column chromatography on silica gel(100-200 mesh) using ethyl acetate (5-10%) in petroleum ether (60-80 C) as the eluent.The ratio of alpha and beta anomers, which had close Rf values and eluted together, was determined by integration of the corresponding hydrogen signals in the 1HNMR of the crude product.
(2R,3R,4S)-2-(acetoxymethyl)-5-((2,4,6-trimethoxybenzoyl)oxy)-3,4-dihydro-2H-pyran-3,4-diyl diacetate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
86%
With [bis(acetoxy)iodo]benzene; palladium diacetate; In acetonitrile; at 120℃; for 12h;Sealed tube;
General procedure: To a stirred solution of tri-O-acetyl-D-glucal (0.5 mmol), palladium acetate (0.025 mmol), PhI(OAc)2 (0.5 mmol) was added aromatic acid (1 mmol). The resulting mixture was heated in a sealed tube at 120 C in dry acetonitrile (10 mL) for 12h. After completion, the solvent was removed under reduced pressure and diluted with ethyl acetate (2 mL), washed with aqueous NaHCO3 (5 mL) followed by water and brine solution (5 mL). The organic layer was evaporated and the residue was purified by flash column chromatography (hexane/EtOAc = 7/3) to afford the product as a colorless oil.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
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120K+ Compounds
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