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. 2024 Oct 31;9(45):45047-45052.
doi: 10.1021/acsomega.4c05247. eCollection 2024 Nov 12.

One-Pot Stereospecific Synthesis of 1,4-Oligosaccharides by Glycal-Derived Vinyl Epoxides Assembly

Maria Chiara Santangelo  1 , Dalila Iacopini  1 , Lucilla Favero  1 , Riccardo Zecchi  2 , Giuseppe Pieraccini  2 , Sebastiano Di Pietro  1 , Valeria Di Bussolo  1
Affiliations

One-Pot Stereospecific Synthesis of 1,4-Oligosaccharides by Glycal-Derived Vinyl Epoxides Assembly

Maria Chiara Santangelo et al. ACS Omega. .

Abstract

Recently, naturally occurring linear 1,4-glycans have attracted remarkable attention for their activity in cancer and neurodegenerative disease treatment. Classical chemical synthetic strategies for linear 1,4-oligosaccharides are considerably time-consuming due to orthogonal protection/deprotection, the introduction of leaving groups, and various forms of activation of the glycosylation reaction. Herein, we present a new one-pot microwave-activated reiterative assembly of glycal-derived vinyl epoxides in an uncatalyzed substrate-dependent stereospecific process for the preparation of both β-1,4-d-Gulo and α-1,4-d-Manno oligosaccharides.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Reiterative Assembly of Vinyl Epoxides 1α and 2β
Scheme 2
Scheme 2. Microwave-Activated Reiterative Assembly of Vinyl Epoxide 2β with Initiator 3β
Figure 1
Figure 1
NOESY map for penta-3β with key NOE effects highlighted.
Scheme 3
Scheme 3. Dihydroxylation of penta-3β
Scheme 4
Scheme 4. Reiterative Assembly of Vinyl Epoxide 1α with Initiator 3α
Scheme 5
Scheme 5. Dihydroxylation of tri-3α
Scheme 6
Scheme 6. Synthesis of Disaccharide 10α
See this image and copyright information in PMC

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