Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Improved Synthesis of 2-Deoxy-2-fluoro-D-glucose Using Fluoride Ion
原田平 輝志前田 稔甲斐 康信尾前 裕子小嶋 正治
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キーワード: 2-deoxy-2-fluoro-D-glucose
ジャーナル フリー

1985 年 33 巻 1 号 p. 165-172

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抄録
Methyl 3-O-benzyl-4, 6-O-benzylidene-2-O-(trifluoromethanesulfonyl)-β-D-mannopyranoside (7) was examined as a substrate for the preparation of 2-deoxy-2-fluoro-D-glucose (1) by fluoride ion treatment. The triflate (7) reacted rapidly with tetraalkylammonium fluorides in acetonitrile or tetrahydrofuran to give methyl 3-O-benzyl-4, 6-O-benzylidene-2-deoxy-2-fluoro-β-D-glucopyranoside (10) in 52-57% yield. Removal of the protecting groups from 10 by the use of 50% methanesulfonic acid afforded the required 1 in good yield. This synthetic sequence may provide an effective alternative to known methods for preparing 18F-labeled 1.
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© The Pharmaceutical Society of Japan
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