Synthesis of glycosyl chlorides using catalytic Appel conditions

Pongener, Imlirenla; Nikitin, Kirill; McGarrigle, Eoghan M.

Abstract

The stereoselective synthesis of glycosyl chlorides using catalytic Appel conditions is described. Good yields of α-glycosyl chlorides were obtained using a range of glycosyl hemiacetals, oxalyl chloride and 5 mol% Ph3PO. For 2-deoxysugars treatment of the corresponding hemiacetals with oxalyl chloride without phosphine oxide catalyst also gave good yields of glycosyl chloride. The method is operationaly simple and the 5 mol% phosphine oxide by-product can be removed easily. Alternatively a one-pot, multi-catalyst glycosylation can be carried out to transform the glycosyl hemiacetal directly to a glycoside.

Citation

Pongener, I., Nikitin, K., & McGarrigle, E. M. (in press). Synthesis of glycosyl chlorides using catalytic Appel conditions. Organic and Biomolecular Chemistry, 17(32), 7531-7535. https://doi.org/10.1039/c9ob01544b

• Journal Article Type: Article
• Acceptance Date: Jul 26, 2019
• Online Publication Date: Aug 1, 2019
• Deposit Date: Jun 16, 2023
• Journal: Organic & Biomolecular Chemistry
• Print ISSN: 1477-0520
• Electronic ISSN: 1477-0539
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 17
• Issue: 32
• Pages: 7531-7535
• DOI: https://doi.org/10.1039/c9ob01544b
• Keywords: Organic Chemistry; Physical and Theoretical Chemistry; Biochemistry
• Additional Information: : This document is Similarity Check deposited; : Supplementary Information; : Imlirenla Pongener (ORCID); : Kirill Nikitin (ORCID); : Eoghan M. McGarrigle (ORCID); : Single-blind; : Received 11 July 2019; Accepted 26 July 2019; Advance Article published 1 August 2019; Version of Record published 14 August 2019