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

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.