Simple Synthesis of (-)-Deoxymannojirimycin and (2S,3R,4R,5R)-3,4,5-trihydroxypipecolic Acid via Regioselective Hydrolysis

DOI: 10.1039/P19940002621

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2621 - 2624 (1994)

Update date:2022-08-04

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Authors:

Park, Ki Hun

Yoon, Yong Jin

Lee, Sang Gyeong

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Article abstract of DOI:10.1039/P19940002621

A short and efficient synthesis of (-)-deoxymannojirimycin and (2S,3R,4R,5R)-3,4,5-trihydroxypipecolic acid is described with D-glucono-δ-lactone as chiral educt.Key transformations included selective cleavage of a terminal isopropylidene group with Dowex 50W-X8 (H⁺) and intramolecular nucleophilic amination.

Full text of DOI:10.1039/P19940002621

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Product name:methyl 2-benzyloxycarbonylamino-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate

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