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 5 publications

(1 citation statement)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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

Self Cite

View full text Add to dashboard Cite

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.

show abstract