Synthesis of 7-O-galloyl-D-sedoheptulose.
A facile synthetic approach to 7-O-galloyl-D-sedoheptulose (1), a natural product with notable immunosuppressant activity, was developed. The starting material, 2,7-anhydro-d-sedoheptulose (2), was converted in three steps into 1,3,4,5-tetra-O-benzyl-d-sedoheptulose (5), a key intermediate that allows specific functionalization at C-7 of the sedoheptulpyranose. After regioselective esterification of 5 with 3,4,5-tri-O-benzyl galloyl acid, followed by catalytic debenzylation (Pd-C), 1 was obtained in an overall yield of 60%. The spectroscopic data and TLC behavior of 1 were found to be identical to that of the natural product.
Xie
Yupeng
Y
Beijing Institute of Pharmacology and Toxicology, 27 Taiping Road, 100850 Beijing, China.
Zhao
Yimin
Y
D029768:Cornus / Q000737:chemistry; D005707:Gallic Acid / Q000737:chemistry*; D006539:Heptoses / Q000138:chemical synthesis* / Q000737:chemistry*
D006539:Heptoses; C003011:sedoheptulose; D005707:Gallic Acid