Chemoenzymatic Synthesis of arabino-Configured Bicyclic Nucleosides

Harbansh Singla; Jyotirmoy Maity; Sandeep Kumar; Kavita Kavita; Riya Chaudhary; Ashok K. Prasad

doi:10.1055/s-0041-1738440

Synthesis, Inhaltsverzeichnis

Synthesis 2024; 56(06): 1035-1041
DOI: 10.1055/s-0041-1738440

paper

Emerging Trends in Glycoscience

Chemoenzymatic Synthesis of arabino-Configured Bicyclic Nucleosides

Autor*innen

Harbansh Singla

^aBioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India
Jyotirmoy Maity

^bDepartment of Chemistry, St. Stephen’s College, University of Delhi, Delhi 110 007, India
Sandeep Kumar

^aBioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India
Kavita Kavita

^aBioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India
Riya Chaudhary

^aBioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India
Ashok K. Prasad ∗

^aBioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India

Abstract

Alle Artikel dieser Rubrik

Abstract

A convergent route for the synthesis of a new class of bicyclic nucleosides has been developed. The synthetic route to the corresponding arabino-configured uracil and thymine bicyclic nucleosides proceeds in 24 and 27% overall yields, respectively, starting from 1,2,5,6-di-O-isopropylidene-α-d-glucofuranose. This synthetic protocol includes some crucial steps such as Vorbrüggen base coupling and chemo-enzymatic regioselective acetylation of the primary hydroxyl group by using Lipozyme^® TL IM where it was found that Lipozyme^® TL IM could be recovered and reused for selective acetylation without losing its selectivity.

Key words

chemo-enzymatic pathway - regioselective monoacetylation - Lipozyme^® TL IM - bicyclic nucleosides

Volltext

Referenzen

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Zusatzmaterial

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