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Synthesis of 6‐amino‐6‐ 14 C‐hexyl 1‐thio‐α‐D‐mannopyranoside
Author(s) -
Durette Philippe L.,
Ellsworth Robert L.,
Shen T. Y.
Publication year - 1980
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.2580170114
Subject(s) - chemistry , thio , nitrile , amine gas treating , sodium cyanide , derivative (finance) , nucleophile , stereochemistry , medicinal chemistry , trimethylsilyl cyanide , cyanide , catalysis , organic chemistry , financial economics , economics
The radiolabeled insulin‐like carbohydrate derivative, 6‐amino‐6‐ 14 C‐hexyl 1‐thio‐α‐D‐mannopyranoside ( 6 ), has been synthesized for receptor binding and mechanism‐of‐action studies by a two‐step process from 5‐bromopentyl 1‐thio‐α‐D‐mannopyranoside (4). Nucleophilic displacement reaction on compound 4 with sodium cyanide‐ 14 C and subsequent catalytic reduction of the intermediate nitrile 5 afforded after chromatography the radiochemically pure amine 6 with a specific activity of 47·3 mCi/mmol.
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