Deoxy‐nitrosugars. 10th Communication. Synthesis of Isosteric Phosphonate Analogues of Ulose‐1‐Phosphates

Abstract

Abstract A general approach to isosteric phosphonate analogues of ulose‐l‐phosphates is described. A base‐catalysed chain elongation via a Michael addition of 1‐deoxy‐1‐nitro‐sugars 4, 8 , and 16 to the vinylphosphonate 18 followed by hydrolysis of the nitro adducts gave the analogues of D ‐ribulose‐1‐phosphate, D ‐fructose‐1‐phosphate, and D ‐sedoheptulose‐1,7‐diphosphate 21, 23 , and 27 , respectively, in high yields.