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Synthesis and Reactions of 1,4‐Anhydrogalactopyranose and 1,4‐Anhydroarabinose – Steric and Electronic Limitations
Author(s) -
Nokami Toshiki,
Werz Daniel B.,
Seeberger Peter H.
Publication year - 2005
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200590224
Subject(s) - chemistry , protonation , steric effects , ring (chemistry) , scope (computer science) , combinatorial chemistry , computational chemistry , electronic effect , stereochemistry , organic chemistry , ion , computer science , programming language
Scope and limitations of 1,4‐anhydro sugars as precursors of glycofuranosyl building blocks are described. The experiments revealed that the choice of the substituents is very important for an efficient preparation as well as a successful ring‐opening reaction of 1,4‐anhydro sugars. DFT Calculations suggest that selective protonation of 1,4‐anhydro sugars is the key to the selective ring opening in order to afford only furanosides.