Novel and facile synthesis of furanodictines A and B based on transformation of 2-acetamido-2-deoxy-D-glucose into 3,6-anhydro hexofuranoses.
A novel synthesis of furanodictines A [2-acetamido-3,6-anhydro-2-deoxy-5-O-isovaleryl-D-glucofuranose (1)] and B [2-acetamido-3,6-anhydro-2-deoxy-5-O-isovaleryl-D-mannofuranose (2)] is described starting from 2-acetamido-2-deoxy-D-glucose (GlcNAc). The synthetic protocol is based on deriving the epimeric bicyclic 3,6-anhydro sugars [2-acetamido-3,6-anhydro-2-deoxy-D-glucofuranose (4) and 2-acetamido-3,6-anhydro-2-deoxy-D-mannofuranose (5)] from GlcNAc. Reaction with borate upon heating led to a facile transformation of GlcNAc into the desired epimeric 3,6-anhydro sugars. The C5 hydroxyl group of the 3,6-anhydro compounds 4 and 5 was regioselectively esterified with the isovaleryl chloride to complete the synthesis of furanodictines A and B, respectively. The targets 1 and 2 were synthesized in only two steps requiring no protection/deprotection.
Ogata
Makoto
M
Department of Bioscience, Graduate School of Science and Technology, Shizuoka University, Ohya 836, Suruga ward, Shizuoka 422-8529, Japan.
Hattori
Takeshi
T
Takeuchi
Ryota
R
Usui
Taichi
T
D000117:Acetylglucosamine / Q000737:chemistry*; D000606:Amino Sugars / Q000138:chemical synthesis*; D001881:Borates / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D007700:Kinetics
D000606:Amino Sugars; D001881:Borates; D005663:Furans; C459700:furanodictine A; C459701:furanodictine B; D000117:Acetylglucosamine