Catalyst-free regioselective acetylation of primary hydroxy groups in partially protected and unprotected thioglycosides with acetic acid-Reference-Cited by-同舟云学术

Catalyst-free regioselective acetylation of primary hydroxy groups in partially protected and unprotected thioglycosides with acetic acid

Published:2020 Issue:60 Volume:10 Page:36836-36842
ISSN:2046-2069
Container-title:RSC Advances
language:en
Short-container-title:RSC Adv.

Author:

Abronina Polina I.¹²³⁴^ORCID,Malysheva Nelly N.¹²³⁴,Zinin Alexander I.¹²³⁴,Kolotyrkina Natalya G.¹²³⁴,Stepanova Elena V.¹²³⁴⁵^ORCID,Kononov Leonid O.¹²³⁴^ORCID

Affiliation:

1. N. K. Kochetkov Laboratory of Carbohydrate Chemistry

2. N. D. Zelinsky Institute of Organic Chemistry

3. 119991 Moscow

4. Russian Federation

5. Research School of Chemistry and Applied Biomedical Sciences

Abstract

Highly regioselective acetylation of primary hydroxy groups in thioglycoside derivatives was achieved by treatment with aqueous or anhydrous acetic acid (60–100%) at elevated temperatures (80–118 °C), avoiding manipulations with protective groups.

Funder

Russian Foundation for Basic Research

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemical Engineering,General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2020/RA/D0RA07360A

Reference80 articles.

1. S.Oscarson , in The Organic Chemistry of Sugars , ed. D. E. Levy and P. Fügedi , CRC Press, Taylor & Francis Group , Boca Raton, FL , 2005 , pp. 73–107

2. Site-Selective Functionalization of Hydroxyl Groups in Carbohydrate Derivatives

3. Progress on Selective Acylation of Carbohydrate Hydroxyl Groups

4. Synthesis of carbohydrate building blocks via regioselective uniform protection/deprotection strategies

5. Protecting Groups: Strategies and Applications in Carbohydrate Chemistry , ed. S. Vidal , Wiley-VCH Verlag GmbH & Co. KGaA , Weinheim , 2019

Cited by 6 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. TsOH-catalyzed acyl migration reaction of the Bz-group: innovative assembly of various building blocks for the synthesis of saccharides;Organic & Biomolecular Chemistry;2023

2. Acetyl Group Migration in Xylan and Glucan Model Compounds as Studied by Experimental and Computational Methods;The Journal of Organic Chemistry;2022-10-17

3. Stereocontrolling Effect of a Single Triisopropylsilyl Group in 1,2‐ cis ‐Glucosylation;European Journal of Organic Chemistry;2022-07-18

4. Trifluoroacetic Acid Promoted Ring Contraction in 2,3-Di-O-silylated O-Galactopyranosides and Hemiacetals;Synlett;2022-01-04

5. The Influence of Anomeric Configuration and Aglycone Structure on the Outcome of Acid‐Promoted Ring Contraction in 2,3‐Di‐ O ‐Silylated S‐Galactopyranosides;ChemistrySelect;2021-06-25