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1.
Org Lett ; 25(43): 7873-7877, 2023 11 03.
Artigo em Inglês | MEDLINE | ID: mdl-37862141

RESUMO

A synthetic route to 2,4-diamino-2,4,6-trideoxysugar stereoisomers in 6-7 steps and 22-33% overall yield is described. A key step in this pathway is the carbonyl coupling of d- and l-threoninol or d- and l-allo-threoninol to a phthalimido-allene mediated by chiral iridium-H8-BINAP, which allows for installation of two new chiral centers in one, highly diastereoselective (>20:1 dr) step. This approach provides a more concise, diastereoselective, and versatile method to access these deoxy-amino sugars than is currently available.


Assuntos
Amino Álcoois , Amino Açúcares , Butileno Glicóis , Estereoisomerismo
2.
Angew Chem Int Ed Engl ; 60(43): 23171-23175, 2021 10 18.
Artigo em Inglês | MEDLINE | ID: mdl-34463017

RESUMO

An automated continuous flow system capable of producing protected deoxy-sugar donors from commercial material is described. Four 2,6-dideoxy and two 3-amino-2,3,6-trideoxy sugars with orthogonal protecting groups were synthesized in 11-32 % overall yields in 74-131.5 minutes of total reaction time. Several of the reactions were able to be concatenated into a continuous process, avoiding the need for chromatographic purification of intermediates. The modular nature of the experimental setup allowed for reaction streams to be split into different lines for the parallel synthesis of multiple donors. Further, the continuous flow processes were fully automated and described through the design of an open-source Python-controlled automation platform.


Assuntos
Amino Açúcares/síntese química , Desoxiaçúcares/síntese química , Monossacarídeos/síntese química
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