D‐glucose derivatives labelled with ^75,77Br and ¹²³I

Abstract

Abstract Synthetic routes to D‐glucose derivatives labelled with either the positron emitter 75 Br (T 1/2 = 1.6 hr) or the single photon emitters 77 Br (T 1/2 = 56 hr) and 123 I (T 1/2 = 13.3 hr) in positions 2 or 3 were investigated in order to prepare useful tracers for glucose utilization studies in brain and heart. 3‐Deoxy‐3‐iodo‐D‐glucose and 3‐deoxy‐3‐bromo‐D‐glucose were prepared from 1,2:5,6‐di‐isopropylidene‐D‐allose via its triflate in 10‐20 % radiochemical yield. 2‐Deoxy‐2‐iodo‐D‐glucose and 2‐deoxy‐2‐bromo‐D‐glucose could not be prepared by the routes presented in this publication. On the route to these compounds, some intermediates of possible use as tracers for glucose utilization were prepared, namely the methyl glucosides methyl 2‐deoxy2‐iodo‐β‐D‐glucopyranoside (MIDG) and methyl 2‐deoxy‐2‐bromo‐β‐D‐glucopyranoside (MBDG) and the acetylated methyl glucosides methyl 3,4,6‐tri‐O‐acetyl‐2‐deoxy‐2‐iodo‐β‐D‐glucopyranoside (MTIG) and methyl 3,4,6‐tri‐O‐acetyl‐2‐deoxy‐2‐bromo‐β‐D‐glucopyranoside (MTBG). Radiochemical yields from 3,4,6‐tri‐O‐acetyl‐D‐glucal, halide ion and dichloramin T were 35 % for MTBG, 40 % for MTIG, 15 % for MBDG and 20 % for MIDG. Preparation times were less than 2 hours.