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Regioselective Dehydration of Sugar Thioacetals under Mild Conditions

Szpara, R; Goyder, A; Porter, MJ; Hailes, HC; Sheppard, TD; (2021) Regioselective Dehydration of Sugar Thioacetals under Mild Conditions. Organic Letters 10.1021/acs.orglett.1c00424. (In press). Green open access

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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.

Type: Article
Title: Regioselective Dehydration of Sugar Thioacetals under Mild Conditions
Location: United States
Open access status: An open access version is available from UCL Discovery
DOI: 10.1021/acs.orglett.1c00424
Publisher version: https://dx.doi.org/10.1021/acs.orglett.1c00424
Language: English
Additional information: This version is the version of record. The article has been published under the CC BY licence.
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10124427
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