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patent

Method for preparing an acetal-protected sugar

Hedou, Maxime  
•
Marti, Roger
•
Nelis, Tom  
Show more
2025

Method for preparing an acetal-protected sugar involving the step of reacting a diol group of a sugar selected from the group consisting of an aldopentose and an aldohexose with one or two compounds of formula (Ia) and/or (Ib) in the presence of a homogenous or heterogenous catalyst to form an acetal-protected sugar selected from the group consisting of a compound of formula (II), (III) and (IV) wherein R1 and/or R2 are independent from each other -Z-X, and wherein Z is a linear, branched or cyclic hydrocarbon moiety with 1 to 10 carbon atoms, optionally substituted with 1 to 4 C1- C4-alkyl groups or 1 to 4 halogen atoms, or -B-D, wherein B is a linear hydrocarbon moiety with 1 to 3 carbon atoms and may be present or absent, D is an aromatic moiety having 6 carbon atoms, optionally substituted with 1 to 4 C1-C4-alkyl groups, 1 to 2 -OH groups, 1 to 2 -OCH3 groups or 1 to 4 halogen atoms and combinations thereof, and wherein Z may be present or absent, and X is -COOH, -CH(COOH)2, -COOR3, CHO, -C2H3, -C2H, -CHOR4OR5, - N3, -NHR6, -NR7R8, -F, -Cl, -Br, -I, or if Z is present, -OH, NH2, or -SH; R3, R4 and R5 are independently selected from the group consisting of a linear, branched or cyclic hydrocarbon moiety having 1 to 20 carbon atoms, optionally substituted with 1 to 4 C1 to C4 alkyl groups and/or 1 to 4 halogen atoms selected from the group consisting of fluoro, chloro, bromo and iodo; R6 is a C1-C4-alkyl group; R7, R8 and R9 are independently from each other a C1-C4-alkyl group; R30 and R31 are independently selected from the group consisting of hydrogen and a linear or branched hydrocarbon moiety having 1 to 4 carbon atoms, with the proviso that R30 and R31 cannot both be hydrogen; R10 is selected from the group consisting of -H, -OH, - CH2OH, -OR13 or -CH2OR14; R11 and R12 are independently selected from the group consisting of -OH or -OR13; R13 and R14 are independently selected from a hydrocarbon moiety with 1 to 10 carbon atoms; and n and p are independently from each other either 0 or 1.

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Type
patent
EPO Family ID

87340781

Author(s)
Hedou, Maxime  
Marti, Roger
Nelis, Tom  
Cattaneo, Alessandro
Manker, Lorenz  
Luterbacher, Jeremy  
Issuers

École Polytechnique Fédérale de Lausanne

Note

Alternative title(s) : (fr) Procédé de préparation d'un sucre protégé par un acétal

EPFL units
AVP-R-TTO  
IdentifierCountry codeKind codeDate issued

WO2025016942

WO

A1

2025-01-23

Available on Infoscience
February 3, 2025
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/246400
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