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Regioselective Dehydration of Sugar Thioacetals under Mild Conditions.

ABSTRACT: Sugars are abundant in waste biomass, making them sustainable chiral building blocks for organic synthesis. The demand for chiral saturated heterocyclic rings for pharmaceutical applications is increasing as they provide well-defined three-dimensional frameworks that show increased metabolic resistance. A range of sugar thioacetals can be dehydrated selectively at C-2 under mild basic conditions, and the resulting ketene thioacetals can be applied to the production of useful chiral building blocks via further selective dehydration reactions.

SUBMITTER: Szpara R

PROVIDER: S-EPMC8041386 | biostudies-literature | 2021 Apr

REPOSITORIES: biostudies-literature

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Regioselective Dehydration of Sugar Thioacetals under Mild Conditions.

Szpara Rachel R Goyder Alexander A Porter Michael J MJ Hailes Helen C HC Sheppard Tom D TD

Organic letters 20210317 7

Sugars are abundant in waste biomass, making them sustainable chiral building blocks for organic synthesis. The demand for chiral saturated heterocyclic rings for pharmaceutical applications is increasing as they provide well-defined three-dimensional frameworks that show increased metabolic resistance. A range of sugar thioacetals can be dehydrated selectively at C-2 under mild basic conditions, and the resulting ketene thioacetals can be applied to the production of useful chiral building bloc ...[more]

PMID: 33729808

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