Synthesis of 1-Deoxymannojirimycin from D-Fructose using the Mitsunobu Reaction
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Jenkins, Ian D
Houston, Todd A
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Abstract
Three different Mitsunobu reactions have been investigated for the synthesis of 1-deoxymannojirimycin (1-DMJ) from d-fructose. The highest yielding and most practical synthesis can be undertaken on a 10 g scale with minimal chromatography. In the key step, N,O-di-Boc-hydroxylamine reacts with methyl 1,3-isopropylidene-α-d-fructofuranose under Mitsunobu conditions to give 14. Acidic hydrolysis affords nitrone 15, which reduces quantitatively via catalytic hydrogenolysis to afford 1-DMJ (4) in 55% overall yield from d-fructose (cf. 37% for azide route and 29% for nosyl route).
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The Journal of Organic Chemistry
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87
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24
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This document is the Postprint: Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright 2022 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://doi.org/10.1021/acs.joc.2c02174
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Subject
Inorganic chemistry
Medicinal and biomolecular chemistry
Organic chemistry
Science & Technology
Physical Sciences
Chemistry, Organic
Chemistry
ENZYME-CATALYZED REACTIONS
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Sunde-Brown, P; Jenkins, ID; Houston, TA, Synthesis of 1-Deoxymannojirimycin from D-Fructose using the Mitsunobu Reaction, The Journal of Organic Chemistry, 2022, 87 (24), pp. 16895-16901