A Preparative Synthesis of Human Chitinase Fluorogenic Substrate (4′-Deoxychitobiosyl)-4-methylumbelliferone

To meet the increasing clinical demand for the diagnostic agent (4′‐deoxychitobiosyl)‐4‐methylumbelliferone, a flexible and scalable route of synthesis is needed. In this paper such a route is presented. The key to the route is the use of a partially protected thiophenyl glucosamine as starting material for the preparation of both the reducing and nonreducing end building blocks of the 4′‐deoxychitobiose disaccharide. The increased awareness of the involvement of chitinase in several human diseases has led to an increased demand of (4′‐deoxychitobiosyl)‐4‐methylumbelliferone. A flexible and scalable route of synthesis is presented for the construction of this diagnostic probe.