Expedient synthesis of 1,6-anhydro-α-D-galactofuranose, a useful intermediate for glycobiological tools

• Luciana Baldoni and
• Carla Marino

Beilstein J. Org. Chem. 2014, 10, 1651–1656, doi:10.3762/bjoc.10.172

• three-step procedure for the synthesis of 1,6-anhydro-α-D-galactofuranose is described. The key step involves the formation of the galactofuranosyl iodide by treatment of per-O-TBS-D-Galf with TMSI, the selective 6-O-desilylation by an excess of TMSI, and the simultaneous nucleophilic attack of the 6

• ][31]. Our laboratory has long been involved in the development of new galactofuranosyl derivatives and galactofuranosylation methodologies [32]. In this context, we herein report on an efficient three-step synthesis of 1,6-anhydro-α-D-galactofuranose (2) from per-O-TBS-β-D-galactofuranose (9) as a

• showed 1H and 13C NMR spectra coincident with the data reported for 1,6-anhydro-α-D-galactofuranose (2) [16][37]. With the objective of optimizing the conditions for glycosylations via iodide 10, the formation of 12 was suppressed by strict control of the TMSI amount employed. Taking into consideration

Synthesis of a derivative of α-D-Glcp(1->2)-D-Galf suitable for further glycosylation and of α-D-Glcp(1->2)-D-Gal, a disaccharide fragment obtained from varianose

• Carla Marino,
• Carlos Lima,
• Karina Mariño and
• Rosa M. de Lederkremer

Beilstein J. Org. Chem. 2012, 8, 2142–2148, doi:10.3762/bjoc.8.241

• monitor the natural disaccharide released from varianose by mild acid degradation. The synthesis, performed by the glycosylaldonolactone approach, involved a glucosylgalactofuranose derivative, suitable for the synthesis of higher oligosaccharides with an internal D-Galf. Keywords: α-D-galactofuranose