Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Review
. 2019 May 28;17(20):4934-4950.
doi: 10.1039/c9ob00573k. Epub 2019 May 2.

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

Tinghua Wang  1 , Alexei V Demchenko  1
Affiliations
Review

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

Tinghua Wang et al. Org Biomol Chem. .

Abstract

Discussed herein is the synthesis of partially protected carbohydrates by manipulating only one type of a protecting group for a given substrate. The first focus of this review is the uniform protection of an unprotected starting material in a way that only one (or two) hydroxyl group remains unprotected. The second focus involves regioselective partial deprotection of uniformly protected compounds in a way that only one (or two) hydroxyl group becomes liberated.

PubMed Disclaimer

Figures

Scheme 1.
Scheme 1.
The overview of protecting group strategies described herein
Scheme 2.
Scheme 2.
Partial acetylation of methyl α-D-glucopyranoside 1 provides a mixture of products
Scheme 3.
Scheme 3.
Regioselective benzoylation
Scheme 4.
Scheme 4.
Examples of regioselective acetylation
Scheme 5.
Scheme 5.
Reagent-dependent tin-mediated acetylation
Scheme 6.
Scheme 6.
Regioselective protection with pivaloyl groups
Scheme 7.
Scheme 7.
Regioselective alkylation and silylation
Scheme 8.
Scheme 8.
Double ketal protection of hexoses
Scheme 9.
Scheme 9.
Examples of regioselective deacetylation
Scheme 10.
Scheme 10.
The synthesis of 2-OH derivatives
Scheme 11.
Scheme 11.
Examples of regioselective primary debenzylation
Scheme 12.
Scheme 12.
Examples of regioselective secondary debenzylation
Scheme 13.
Scheme 13.
Regioselective removal of PMB groups
Scheme 14.
Scheme 14.
Regioselective desilylation
Scheme 15.
Scheme 15.
Regioselective deprotection of isopropylidene
Scheme 16.
Scheme 16.
Reductive opening of benzylidene acetals
Scheme 17.
Scheme 17.
Regioselective ring opening of other cyclic groups.
See this image and copyright information in PMC

References

    1. Oscarson S: Protective group strategies In The organic chemistry of sugars; Levi DE, Fugedi P, Eds.; CRC, Taylor & Francis: Boca Raton - London - New York, 2006; pp 53–88.
    1. Wuts PGM; Greene TW: Greene’s Protective Groups in Organic Synthesis; 4th ed.; Wiley-Interscience, 2007.
    1. Polyakova SM; Nizovtsev AV; Kuznetskiy RA; Bovin NV New protecting groups in oligosaccharide syntehsis. Russ. Chem. Bull 2015, 974–989.
    1. Volbeda AG; van der Marel GA; Codée JDC: Protecting Group Strategies in Carbohydrate Chemistry In Protecting Groups – Strategies and Applications in Carbohydrate Chemistry; Vidal S, Ed.; Wiley-VCH: Weinheim, 2019; pp 1–28.
    1. Ágoston K; Streicher H; Fügedi P Orthogonal protecting group strategies in carbohydrate chemistry. Tetrahedron: Asymmetry 2016, 27, 707–728.

Publication types

MeSH terms