308140-72-9Relevant academic research and scientific papers
De novo asymmetric synthesis of protected 5-O-carbamoylpolyoxamic acid
Dehoux,Monthieu,Baltas,Gorrichon
, p. 1409 - 1414 (2007/10/03)
The synthesis of 5-O-carbamoylpolyoxamic acid from a non carbohydrate precursor was achieved in 12 steps and 7% yield starting from chiral α,β-epoxyaldehyde readily available from cis-2-butene-1,4-diol. The main steps concern the Sharpless asymmetric epoxidation of a suitable chosen allylic alcohol, the use of thiazolyl group for carbon homologation, the stereo- and regioselective opening of the epoxide and the transformation of the primary alcohol to the acid functionality of the final product.
