The present invention relates to a process for preparing an at least partially
acetal-protected
sugar, comprising the step of reacting a
sugar or
sugar derivative selected from the group consisting of aldopentoses, aldohexoses, aldopentosides and aldohexosides with an
aldehyde or
aldehyde source in the presence of a heterogeneous acidic catalyst to form an at least partially
acetal-protected sugar selected from the group consisting of compounds of formula (I), (II), (III), (IV), (V), (VI), (VII), (VIII), (IX), (X), (XI) and (XII): In the formula, R1, R1', R2, R2', R3, R3', R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 and R 12 and R and R′, R and R′, R and R′, and R 12 and R 12 are identical or different from one another; and Y is
hydrogen or a straight, branched, or
cyclic hydrocarbon moiety having 1 to 20 carbon atoms; Z is a linear, branched, or
cyclic hydrocarbon moiety having 0 to 12 carbon atoms, optionally substituted with 1 to 4 C1-C4
alkyl groups, or 1 to 4
halogen atoms, or a
benzyl group; and E is -COOH, -CH(COOH)2, -COOR 19 , -CH(COOR 20 )(COOR 21 ), -CHO, -CH(CHO)2, -C2H3, -CH(C2H3)2, -CHCHR 22 , -CHCR 23 R 24 , -C2H, -C2R 25 , -N3, -NH2, -CH(NH2)2, -NHR 26 , -CH(NHR 27 )(NHR 28 ), -NR 29 R 30 , -CH(NR 31 R 32 )(NR 33 R 34 ), -OH, -OR35 , or -CH(R 36 OH)(R 37 OH); and R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 and R 35 are C1 to C 20 is
alkyl; and R 20 and R 21 , R 23 and R 24 , R 27 and R 28 , R 29 and R 30 , R 31 and R 32 , and R 33 and R 34 are identical to or different from one another; and R 36 and R 37 are, independently of one another, absent or straight-chain or branched C1-C 12 is a
hydrocarbon chain; and R 13 , R 14 , R 15 , R 16 , R 17 and R 18 are each independently
hydrogen or a straight-chain, branched-chain, or
cyclic hydrocarbon moiety having 1 to 20 carbon atoms.
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