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D‐glucose derivatives labelled with 75,77 Br and 123 I
Author(s) -
Kloster Gerd,
Laufer Peter,
Stöcklin Gerhard
Publication year - 1983
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580200309
Subject(s) - chemistry , d glucose , yield (engineering) , trifluoromethanesulfonate , halide , medicinal chemistry , 2 deoxy d glucose , radiochemistry , stereochemistry , catalysis , organic chemistry , biochemistry , materials science , metallurgy
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.