Automated Solution-Phase Synthesis of beta-1,4-Mannuronate and beta-1,4-Mannan

作者：Tang Shu Lun; Pohl Nicola L B^*

来源：Organic Letters, 2015, 17(11): 2642-2645.

DOI：10.1021/acs.orglett.5b01013

The first automated solution-phase synthesis of beta-1,4-mannuronate and beta-1,4-mannan oligomers has been accomplished by using a beta-directing C-5 carboxylate strategy. By utilizing fluorous-tag assisting purification after repeated reaction cycles, beta-1,4-mannuronate was synthesized up to a hexasaccharide with limited loading of a glycosyl donor (up to 3.5 equiv) for each glycosylation cycle due to the homogeneous solution-phase reaction condition. After a global reduction of the uronates, the beta-1,4-mannan hexasaccharide was obtained, thereby demonstrating a new approach to beta-mannan synthesis.

• 出版日期2015-6-5