Sub-stoichiometric reductive etherification of carbohydrate substrates and one-pot protecting group manipulation.

Org Biomol Chem

Applied Chemistry Department, National Chiao Tung University, 1001, University Road, Hsinchu City, Taiwan.

Published: April 2020

In this study, we report a new reductive etherification procedure for protection of carbohydrate substrates and its application for one-pot preparation of glycosyl building blocks. The reported procedure features the use of polymethylhydrosiloxane (PMHS) as a sub-stoichiometric reducing agent, which prevents the transilylation side reaction and improves the efficiency of the reductive etherification method. Application of the PMHS reductive etherification procedure for one-pot protecting group manipulation are described.

Download full-text PDF

Source
http://dx.doi.org/10.1039/d0ob00252fDOI Listing

Publication Analysis

Top Keywords

reductive etherification
16
carbohydrate substrates
8
one-pot protecting
8
protecting group
8
group manipulation
8
etherification procedure
8
sub-stoichiometric reductive
4
etherification
4
etherification carbohydrate
4
substrates one-pot
4

Similar Publications

Traditional etherification methods, although staples in synthetic chemistry, often fall short in the efficient construction of sterically hindered dialkyl ethers, especially under mild and practical conditions. Recent advances have attempted to address these limitations, typically relying on transition metal catalysts, external reductants, or harsh reaction conditions. In this work, we disclose a novel electrochemical approach that enables the synthesis of sterically hindered ethers from economically relevant and readily accessible alcohols without the need for sacrificial oxidants.

View Article and Find Full Text PDF

Acid catalysed reductive etherification of -propargyl amino alcohols for the stereoselective synthesis of -2,5/2,6-disubstituted morpholines and -2,6/2,7-disubstituted oxazepanes has been developed. Mechanistic studies revealed that terminal alkynols gave morpholines a 6- hydroalkoxylation-isomerization-reduction cascade. Interestingly, an alkyne hydration-cyclization-reduction sequence is found to be involved in the formation of oxazepanes from alkyl substituted internal alkynols.

View Article and Find Full Text PDF

ConspectusAromatic esters are cost-effective, versatile, and commonly used scaffolds that are readily synthesized or encountered as synthetic intermediates. While most conventional reactions involving these esters are nucleophilic acyl substitutions or 1,2-nucleophilic additions─where a nucleophile attacks the carbonyl group, decarbonylative transformations offer an alternative pathway by using the carbonyl group as a leaving group. This transition-metal-catalyzed process typically begins with oxidative addition of the C(acyl)-O bond to the metal.

View Article and Find Full Text PDF

Synthesis of ZSM-5 Zeolite Nanosheets with Tunable Silanol Nest Contents across an Ultra-wide pH Range and Their Catalytic Validation.

Angew Chem Int Ed Engl

June 2024

Department of Chemistry, Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Laboratory of Advanced Materials, Collaborative Innovation Centre of Chemistry for Energy Materials (iChEM), Fudan University, Shanghai, 200433, P. R. China.

Article Synopsis
  • - Researchers successfully synthesized ZSM-5 zeolite nanosheets (Z-5-SCA-X) across a pH range of 4 to 13 without any additional supplements, addressing challenges of acidic zeolite synthesis.
  • - The study revealed that the crystallization of Z-5-SC, an essential component of the zeolite, follows non-classical processes under mild conditions and combines aspects of classical and non-classical processes under high pH.
  • - Results indicate that controlling the pH during synthesis affects the silanol nest content in the zeolite, which significantly improves its catalytic performance, offering a new perspective on zeolite synthesis and functionality.
View Article and Find Full Text PDF

This manuscript describes the development of the first diastereoselective intermolecular synthesis of alkyl ethers via reductive etherification of diverse ketones or aldehydes with alcohols. Key to this development was the use of low-temperature high-throughput experimentation (HTE) technologies that enabled rapid reaction optimizations and parallel synthesis. A broad scope of pharmaceutically relevant substrates was surveyed, which formed alkyl ethers effectively.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!