A practical approach to Dideoxy-1,4- and 1,5-iminopentitols from protected sugar hemiacetals

Jaszczyk, Justyna; Li, Sizhe; Cocaud, Chloé; Nicolas, Cyril; Martin, Olivier R.

doi:10.1016/j.carres.2019.107855

Cited by 4 publications

(1 citation statement)

References 28 publications

(13 reference statements)

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“…With the N,O-acetals (7) in hand, we then explored the addition of benzyl magnesium chloride, or vinylmagnesium bromide onto glycosylamines (SS)-7B, (SR)-7D, (SS)-7D, and (SS)-7G (entries [24][25][26][27][28]. Interestingly, the 1,2-syn aminoalditol compounds were again obtained in good yields (50-84%) as major diastereomers (ca.…”

Section: Addition Reactionsmentioning

confidence: 99%

Stereoselective Synthesis of Iminosugar‐C‐Glycosides through Addition of Organometallic Reagents to N‐tert‐Butanesulfinyl Glycosylamines: A Comprehensive Study

Kamzol,

Neuville,

Cocaud

et al. 2023

Eur J Org Chem

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A comprehensive study of the preparation and reactivity of N‐tert‐butanesulfinyl glycosylamines with simple Grignard and organo lithium reagents in batch vs. continuous flow chemistry is reported. As they readily react as latent imine equivalents with a variety of carbon nucleophiles, these carbohydrate derivatives constitute very useful precursors for the diastereoselective synthesis of bioactive compounds such as iminosugar‐C‐glycosides. A hybrid protocol, involving the addition of benzylmagnesium chloride to a (SR)‐arabinofuranosylamine substrate in flow, at room temperature, combined with a cyclization protocol in batch is also described for the first time. Of note, this semi‐continuous flow process shortens the synthesis of imino‐C‐glycoside scaffolds to a single workday.

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Section: Addition Reactionsmentioning

confidence: 99%

Stereoselective Synthesis of Iminosugar‐C‐Glycosides through Addition of Organometallic Reagents to N‐tert‐Butanesulfinyl Glycosylamines: A Comprehensive Study

Kamzol,

Neuville,

Cocaud

et al. 2023

Eur J Org Chem

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Recent synthetic strategies to access diverse iminosugars

Matassini,

Cardona

2024

Synthetic Strategies in Carbohydrate Chemistry

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Green synthesis of 1,5-dideoxy-1,5-imino-ribitol and 1,5-dideoxy-1,5-imino-dl-arabinitol from natural d-sugars over Au/Al2O3 and SO42−/Al2O3 catalysts

Gao

Fan

2021

Sci Rep

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A green synthetic route for the synthesis of some potential enzyme active hydroxypiperidine iminosugars including 1,5-dideoxy-1,5-imino-ribitol and 1,5-dideoxy-1,5-imino-dl-arabinitol, starting from commercially available d-ribose and d-lyxose was tested out. Heterogeneous catalysts including Au/Al2O3, SO42−/Al2O3 as well as environmentally friendly reagents were employed into several critical reaction of the route. The synthetic route resulted in good overall yields of 1,5-dideoxy-1,5-imino-ribitol of 54%, 1,5-dideoxy-1,5-imino-d-arabinitol of 48% and 1,5-dideoxy-1,5-imino-l-arabinitol of 46%. The Au/Al2O3 catalyst can be easily recovered from the reaction mixture and reused with no loss of activity.

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A practical approach to Dideoxy-1,4- and 1,5-iminopentitols from protected sugar hemiacetals

Cited by 4 publications

References 28 publications

Stereoselective Synthesis of Iminosugar‐C‐Glycosides through Addition of Organometallic Reagents to N‐tert‐Butanesulfinyl Glycosylamines: A Comprehensive Study

Stereoselective Synthesis of Iminosugar‐C‐Glycosides through Addition of Organometallic Reagents to N‐tert‐Butanesulfinyl Glycosylamines: A Comprehensive Study

Recent synthetic strategies to access diverse iminosugars

Green synthesis of 1,5-dideoxy-1,5-imino-ribitol and 1,5-dideoxy-1,5-imino-dl-arabinitol from natural d-sugars over Au/Al2O3 and SO42−/Al2O3 catalysts

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