Publication

Method for preparing an at least partially acetal-protected sugar

Abstract

The present invention relates to a method for preparing an at least partially acetal-protected sugar involving the step of reacting a sugar or a sugar derivative selected from the group consisting of an aldopentose, an aldohexose, an aldopentoside and an aldohexoside with an aldehyde or an aldehyde source in the presence of heterogeneous acidic catalyst to form the at least partially acetal-protected sugar selected from the group consisting of a compound of formula (I), (II), (III), (IV), (V), (VI), (VII), (VIII), (IX), (X,) (XI) and (XII) wherein R1, R1', R2, R2', R3, R3', R4, R5, R6, R7, R8, R9, R10, R11, R12, and R12' are Y or Z-E, and wherein R1 and R1', R2 and R2', R3 and R3', and R12 and R12' are the same or different from each other and Y is hydrogen or a linear, branched or cyclic hydrocarbon moiety having 1 to 20 carbon 69 atoms, Z is a linear, branched or cyclic hydrocarbon moiety with 0 to 12 carbon atoms, optionally substituted with 1 to 4 C1 to C4 alkyl groups, 1 to 4 halogen atoms, or benzyl groups and E is -COOH, - CH(COOH)2, -COOR19, -CH(COOR20)(COOR21), -CHO, -CH(CHO)2, -C2H3, CH(C2H3)2, -CHCHR22, -CHCR23R24, -C2H, -C2R25, -N3, -NH2, -CH(NH2)2, - NHR26, -CH(NHR27)(NHR28), -NR29R30, -CH(NR31R32)(NR33R34), -OH, -OR35, - CH(R36OH)(R37OH), and R19, R20, R21, R22, R23, R24, R25, R26, R27, R28, R29, R30, R31, R32, R33, R34, and R35, are independent from each other C1 to C20 alkyl, and R20 and R21, R23 and R24, R27 and R28, R29 and R30, R31 and R32, as well as R33 and R34 are the same or different from each other, and R36 and R37 are independent from each other absent or a linear or branched C1 to C12 hydrocarbon chain and R13, R14, R15, R16, R17 and R18 are independent from each other hydrogen or a linear, branched or cyclic hydrocarbon moiety having 1 to 20 carbon atoms.

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Related concepts (35)
Organosulfate
In organosulfur chemistry, organosulfates are a class of organic compounds sharing a common functional group with the structure . The core is a sulfate group and the R group is any organic residue. All organosulfates are formally esters derived from alcohols and sulfuric acid () although many are not prepared in this way. Many sulfate esters are used in detergents, and some are useful reagents. Alkyl sulfates consist of a hydrophobic hydrocarbon chain, a polar sulfate group (containing an anion) and either a cation or amine to neutralize the sulfate group.
Carbon
Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon makes up about 0.025 percent of Earth's crust. Three isotopes occur naturally, ^12C and ^13C being stable, while ^14C is a radionuclide, decaying with a half-life of about 5,730 years. Carbon is one of the few elements known since antiquity.
Aldehyde
In organic chemistry, an aldehyde (ˈældᵻhaɪd) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology. Aldehyde molecules have a central carbon atom that is connected by a double bond to oxygen, a single bond to hydrogen and another single bond to a third substituent, which is carbon or, in the case of formaldehyde, hydrogen.
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