One-pot SSA-catalyzed β-elimination: an efficient and inexpensive protocol for easy access to the glycal of sialic acid.

Erickson M Paragas, I Abrrey Monreal, Chris M Vasil, Jonel P Saludes

Abstract read

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Article in Carbohydrate research, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

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2citing papers in PubMed

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3 · Its place in the literature

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2 citing papers in PubMed.

SialoPen peptides are new cationic foldamers with remarkable cell permeability.Heliyon · 2020
Article
SnClBeilstein journal of organic chemistry · 2019
Article

4 · The record

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5 · Who and what money

Authors and funding

4 authors.

Erickson M ParagasDepartment of Chemistry, Washington State University, Pullman, WA 99164, USA.

I Abrrey MonrealDepartment of Chemistry, Washington State University, Pullman, WA 99164, USA.

Chris M VasilDepartment of Chemistry, Washington State University, Pullman, WA 99164, USA.

Jonel P SaludesDepartment of Chemistry, Washington State University, Pullman, WA 99164, USA. Electronic address: jonel.saludes@wsu.edu.

Funding

500 MHZ NMR SPECTROMETER PURCHASES10RR006314 · NCRR · WASHINGTON STATE UNIVERSITY · PI SATTERLEE, JAMES D. · 1991 to 1991

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AQUISITION OF A 600 MHZ NMR SPECTROMETERS10RR012948 · NCRR · WASHINGTON STATE UNIVERSITY · PI EVANS, JEREMY N · 1998 to 1998

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NCRR NIH HHS RR0631401NCRR NIH HHS S10 RR006314NCRR NIH HHS S10 RR012948

6 · The paper itself

Abstract

Neu5Ac2en1Me per-OAc, the fully protected glycal of sialic acid, is a key intermediate in the discovery of therapeutics and diagnostics, including anti-influenza drugs and proteolysis resistant peptidomimetic foldamers. The synthesis of this sialic acid derivative, however, still relies on standard sugar chemistry that utilizes multi-step methodologies. Herein we report a facile and highly efficient microwave-assisted preparation of Neu5Ac1Me using silica sulfuric acid (SSA) as solid-supported acid catalyst that is one- to two-orders of magnitude faster than standard procedures. We also describe the microwave-assisted and SSA-catalyzed one-pot, rapid, solvent free reaction that combines both peracetylation and β-elimination reactions in one step to generate the glycal from Neu5Ac1Me. We coined the term One-pot SSA-catalyzed Technology for β-Elimination Protocol (OneSTEP) to describe this least laborious, most efficient, and practical preparation to date of Neu5Ac2en1Me per-OAc in terms of yield, time, reagent cost, and waste generation.

Indexed as

CatalysisEthersMicrowavesN-Acetylneuraminic AcidSilicon DioxideSulfuric AcidsEthersN-Acetylneuraminic AcidSilicon Dioxidesulfuric acidSulfuric Acids4-epi-Neu5Ac2enAcetic anhydrideMicrowave synthesisNeu5Ac2enSialic acidSilica sulfuric acid

Identifiers

PMID25497336

DOI10.1016/j.carres.2014.09.002

PMCPMC4281274

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.