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Stereoselective synthesis of L-[4-13C]carnitine

✍ Scribed by Clifford J. Unkefer; Deborah S. Ehler

Publisher
John Wiley and Sons
Year
1991
Tongue
French
Weight
328 KB
Volume
29
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The stereoselective synthesis of L‐[4‐^13^C]carnitine was achieved in 5 steps. The label was introduced from K^13^CN into an easily separated diastereomeric pair of 3‐deoxy‐D‐[1‐^13^C]aldohexoses. Reductive amination of the labeled aldohexose yielded the corresponding D‐1‐(dimethylamino)[1‐^13^C]alditol which was oxidized in two steps and alkylated with iodomethane to yield L‐[4‐^13^C]carnitine. The stereochemical integrity at C‐2 of the 3‐deoxy‐D‐[1‐^13^C]glucose precursor was maintained throughout the synthesis of L‐[4‐^13^C]carnitine.

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