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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 20
199
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Articles

Synthesis of new ceramide analogues with allene in the sphingoid backbone

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Pages 3149-3157 | Received 26 Oct 2019, Published online: 02 Aug 2020
 

Abstract

Ceramide is an important sphingolipid which can mediate a diverse range of biological activities. New ceramide analogues with an allene group in the sphingoid backbone were synthesized. The synthesis of the key intermediates involved the LiAlH4 reduction of oxazolidine intermediates via a directed reduction-elimination reaction. Hydrolysis of the oxazolidine, liberation of the amino group, and N-acylation provided new ceramide analogues. These new analogues may provide new resources to study their bioactivities and the structure-activity relationship.

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Additional information

Funding

This work was supported by Foundation of Jiangxi Province Educational Committee (KJLD14079).

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