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1 article(s) from Kumar, Banty

Chemical and chemoenzymatic routes to bridged homoarabinofuranosylpyrimidines: Bicyclic AZT analogues

Sandeep Kumar,
Jyotirmoy Maity,
Banty Kumar,
Sumit Kumar and
Ashok K. Prasad

Beilstein J. Org. Chem. 2022, 18, 95–101, doi:10.3762/bjoc.18.10

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Figure 1: Structure of AZT and representative related bicyclic nucleosides.

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Scheme 1: Retrosynthetic routes for the synthesis of (5′R)-3′-azido-3′-deoxy-2′-O,5′-C-bridged-β-ᴅ-homoarabin...

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Scheme 2: Synthesis of 3′-azido-3′-deoxy-β-ᴅ-allofuranosylthymine (14a) and -uracil (14b).

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Scheme 3: Biocatalytic acetylation of the primary hydroxy group of nucleosides 14a,b.

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Scheme 4: Synthesis of (5'R)-3′-azido-3′-deoxy-2′-O,5′-C-bridged-β-ᴅ-homoarabinofuranosyl nucleosides 9a,b.

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Scheme 5: Chemical synthesis of nucleosides 9a,b starting from diacetone ᴅ-glucofuranose.

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Figure 2: Structure elucidation of (5′R)-3′-azido-3′-deoxy-2′-O,5′-C-bridged-β-ᴅ-homoarabinofuranosylthymine (...

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Scheme 6: a) Plausible mechanism for the synthesis of (5′R)-3′-azido-3′-deoxy-2′-O,5′-C-bridged-β-ᴅ-homoarabi...

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Published 11 Jan 2022

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