Convenient Approach to Access Octa-Glycosylated Porphyrins via “Click Chemistry”

<table>Synthesis of octa-<svg height="16.6625" id="M9" style="vertical-align:-3.56265pt" version="1.1" viewbox="0 0 10 16.6625" width="10" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink">
<g transform="matrix(.017,-0,0,-.017,.062,12.162)"><path d="M558 587q0 -32 -14 -61t-40 -53.5t-48.5 -41t-54.5 -36.5q144 -51 144 -174q0 -55 -43.5 -108t-104.5 -87q-77 -42 -131 -42q-31 0 -54 20t-31 47l11 18q48 -29 108 -29q79 0 119.5 43t40.5 109t-44.5 107.5t-119.5 50.5l22 47q34 1 65 21q96 61 96 157q0 42 -24 67.5
t-62 25.5q-24 0 -43.5 -9t-35 -29.5t-27 -44t-22.5 -63t-19.5 -75.5t-18.5 -91q-57 -294 -68 -380q-26 -190 -35 -200q-26 -31 -97 -37l-4 26q19 9 48 170l77 413q23 121 52.5 187.5t83.5 114.5q70 62 148 62q51 0 88.5 -34t37.5 -91z" id="x1D6FD"></path></g>
</svg>-lactosylated porphyrinatocopper (PorCu-Lac<sub>8</sub>): (i) propargyl bromide, K<sub>2</sub>CO<sub>3</sub>, DMF, r.t., (ii) pyrrole, TFA, CH<sub>2</sub>Cl<sub>2</sub>, r.t., then <i>p</i>-chloranil, r.t.,  (iii) CuBr<sub>2</sub>, ascorbic acid, <svg height="16.6625" id="M10" style="vertical-align:-3.56265pt" version="1.1" viewbox="0 0 10 16.6625" width="10" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink">
<g transform="matrix(.017,-0,0,-.017,.062,12.162)"><path d="M558 587q0 -32 -14 -61t-40 -53.5t-48.5 -41t-54.5 -36.5q144 -51 144 -174q0 -55 -43.5 -108t-104.5 -87q-77 -42 -131 -42q-31 0 -54 20t-31 47l11 18q48 -29 108 -29q79 0 119.5 43t40.5 109t-44.5 107.5t-119.5 50.5l22 47q34 1 65 21q96 61 96 157q0 42 -24 67.5
t-62 25.5q-24 0 -43.5 -9t-35 -29.5t-27 -44t-22.5 -63t-19.5 -75.5t-18.5 -91q-57 -294 -68 -380q-26 -190 -35 -200q-26 -31 -97 -37l-4 26q19 9 48 170l77 413q23 121 52.5 187.5t83.5 114.5q70 62 148 62q51 0 88.5 -34t37.5 -91z" id="x1D6FD"></path></g>
</svg>-lactosyl azide, propylamine, r.t.</table>

International Journal of Carbohydrate Chemistry

sch1

Scheme 1

Scheme 1: Convenient Approach to Access Octa-Glycosylated Porphyrins via “Click Chemistry” 