Regioselective Dehydration of Sugar Thioacetals under Mild Conditions | Zendy

Rachel Szpara | Zendy; Alexander Goyder | Zendy; Michael J. Porter | Zendy; Helen C. Hailes | Zendy; Tom D. Sheppard | Zendy

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Regioselective Dehydration of Sugar Thioacetals under Mild Conditions

Author(s) -

Rachel Szpara,

Alexander Goyder,

Michael J. Porter,

Helen C. Hailes,

Tom D. Sheppard

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.1c00424

Subject(s) - ketene , chemistry , dehydration , regioselectivity , sugar , organic chemistry , biomass (ecology) , combinatorial chemistry , biochemistry , catalysis , oceanography , geology

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.

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