Premium
Synthesis of the Cellulose Model Compound Methyl 4″‐ O ‐Methyl‐ β ‐ D ‐Cellotrioside
Author(s) -
del Carmen Ruiz Ruiz Maria,
Querner Jens,
Adorjan Immanuel,
Kosma Paul,
Rosenau Thomas
Publication year - 2005
Publication title -
macromolecular symposia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.257
H-Index - 76
eISSN - 1521-3900
pISSN - 1022-1360
DOI - 10.1002/masy.200551408
Subject(s) - cellobiose , yield (engineering) , cellulose , chemistry , methyl cellulose , dissolution , organic chemistry , materials science , cellulase , metallurgy
Abstract A high‐yield synthetic route towards methyl 4″‐ O ‐methyl‐ β ‐ D ‐cellotrioside ( 17 ) via cellobioside acceptor 8 and glucosyl fluoride donor 15 was established. The former was synthesized from cellobiose peracetate in 7 steps and 21% overall yield, while the latter was obtained from methyl β ‐ D ‐glucopyranoside in a 6‐step‐synthesis with 19% yield. Glycosidation afforded 13% of α ‐compound besides the desired β ‐isomer (31%). The target compound, being the higher homologue of the recently prepared 4′‐ O ‐methyl‐ β ‐ D ‐cellobioside ( 1 ), is required to study by solid‐state techniques the hydrogen bond network in cellodextrins and cellulose, and its changes upon swelling and dissolution.