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Regio‐ and Stereoselective Transformations of Sucrose at the Terminal Positions
Author(s) -
Jarosz Sławomir,
Mach Mateusz
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200203)2002:5<769::aid-ejoc769>3.0.co;2-f
Subject(s) - chemistry , stereoselectivity , terminal (telecommunication) , sucrose , stereochemistry , organic chemistry , catalysis , telecommunications , computer science
Chemistry of sucrose emphasizing regio‐ and stereoselective transformations performed at the terminal positions (C‐1′ and/or C‐6 and/or C‐6′) is reviewed. 2,2′,3,3′,4‐Penta‐ O ‐benzyl sucrose is proposed as particularly useful substrate for the preparation of modified derivatives such as amines, uronic acids, crown ether analogues with incorporated sucrose backbone, and so‐called “higher sucroses”, i.e. compounds elongated at either “end” by up to 9 carbon atoms. Application of benzyl protecting groups makes possible synthesis of free sucrose analogues by simple removing of the protecting groups by hydrogenolysis without affecting the very labile glycosidic bond.