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A basic system of microoperations and its use - download pdf or read online

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By Belyaev A. K.

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SELECTIVE HYDROXYL PROTECTION AND DEPROTECTION Method 11 [97] Preparation of 2,3-di-O-benzyl-4,6-O-benzylidene-D -galactopyranose. Cat. PdCl2, NaOAc, aqueous AcOH, rt. Notes. Transition-metal catalysed deallylation. A convenient one-pot isomerisation/hydrolysis protocol. Materials. 7 EXPERIMENTAL PROCEDURES 51 Equipment. Round bottomed flask (100 ml) with magnetic stirrer bar Magnetic stirrer Column chromatography equipment Procedure. 6 mmol). Stir the reaction mixture at room temperature until TLC analysis indicates that the starting material has been consumed.

Submit the residue to flash column chromatography (2:1, dichloromethane/methanol) to furnish the debenzylated product as a colourless glassy solid (369 mg, 1 100%). 0 Hz, H-1, 1H). Method 10 [96] Preparation of 4-O-allyl-1,2,3,6-tetra-O-acetyl-a-b-D -glucopyranose. AllOCO2Et, DPPB, cat. Pd2dba3, 60 8C, 2 h. Notes. A convenient one-pot procedure for allylation under neutral conditions. Materials. 4 mmol) irritant Dichloromethane (chromatography solvent) toxic, irritant, possible irreversible effects Methanol (chromatography solvent) highly flammable, toxic irritant Equipment.

2, Allyl ethers). As with acetates, benzoate migration can be used to achieve selective protection and release in ways inaccessible by direct methods. 48, benzoylation took place kinetically at the 3-OH group leaving the 2-OH free, but alkaline isomerisation led to benzoate migration to the 2-position leaving the 3-OH free for further manipulation [66]. Finally, because benzoic acid is an excellent partner in the Mitsunobu reaction, benzoate formation with inversion has been used to prepare protected variants of relatively rare carbohydrates from readily available precursors.

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A basic system of microoperations and its use by Belyaev A. K.

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