Use of Protecting Groups in Carbohydrate Chemistry: An Advanced Organic Synthesis Experiment

1999 ◽  
Vol 76 (1) ◽  
pp. 79 ◽  
Author(s):  
Anna C. Cunha ◽  
Leticia O. R. Pereira ◽  
Maria Cecília B. V. de Souza ◽  
Vitor F. Ferreira
Keyword(s):  
Organic Synthesis ◽  
Protecting Groups ◽  
Carbohydrate Chemistry ◽  
Synthesis Experiment

scholarly journals Biocatalysis with Laccases: An Updated Overview

Catalysts ◽  
2020 ◽  
Vol 11 (1) ◽  
pp. 26
Author(s):  
Ivan Bassanini ◽  
Erica Elisa Ferrandi ◽  
Sergio Riva ◽  
Daniela Monti
Keyword(s):  
Organic Synthesis ◽  
Alcohol Oxidation ◽  
Industrial Processes ◽  
Organic Substrates ◽  
Fine Chemicals ◽  
Multicopper Oxidases ◽  
Carbohydrate Chemistry ◽  
Nucleophilic Substitutions ◽  
Mediator System ◽  
Integrated Processes

Laccases are multicopper oxidases, which have been widely investigated in recent decades thanks to their ability to oxidize organic substrates to the corresponding radicals while producing water at the expense of molecular oxygen. Besides their successful (bio)technological applications, for example, in textile, petrochemical, and detoxifications/bioremediations industrial processes, their synthetic potentialities for the mild and green preparation or selective modification of fine chemicals are of outstanding value in biocatalyzed organic synthesis. Accordingly, this review is focused on reporting and rationalizing some of the most recent and interesting synthetic exploitations of laccases. Applications of the so-called laccase-mediator system (LMS) for alcohol oxidation are discussed with a focus on carbohydrate chemistry and natural products modification as well as on bio- and chemo-integrated processes. The laccase-catalyzed Csp2-H bonds activation via monoelectronic oxidation is also discussed by reporting examples of enzymatic C-C and C-O radical homo- and hetero-couplings, as well as of aromatic nucleophilic substitutions of hydroquinones or quinoids. Finally, the laccase-initiated domino/cascade synthesis of valuable aromatic (hetero)cycles, elegant strategies widely documented in the literature across more than three decades, is also presented.

ChemInform Abstract: PROTECTING GROUPS IN ORGANIC SYNTHESIS. PART 8. CONVERSION OF ALDEHYDES INTO GEMINAL DIACETATES

1983 ◽  
Vol 14 (42) ◽  
Author(s):  
K. S. KOCHHAR ◽  
B. S. BAL ◽  
R. P. DESHPANDE ◽  
S. N. RAJADHYAKSHA ◽  
H. W. PINNICK
Keyword(s):  
Organic Synthesis ◽  
Protecting Groups

Protecting Groups in Carbohydrate Chemistry

1997 ◽  
Vol 74 (11) ◽  
pp. 1297 ◽  
Author(s):  
Sigthór Pétursson
Keyword(s):  
Protecting Groups ◽  
Carbohydrate Chemistry

Protecting Groups

2008 ◽  
Author(s):  
Jie Jack Li ◽  
Chris Limberakis ◽  
Derek A. Pflum
Keyword(s):  
Low Temperature ◽  
Organic Synthesis ◽  
Secondary Alcohol ◽  
Primary Alcohol ◽  
Protecting Groups ◽  
Silyl Ether ◽  
Benzyl Ether ◽  
Protecting Group ◽  
Selective Protection ◽  
Death Taxes

In his book, Protecting Groups, Philip J. Kocieński stated that there are three things that cannot be avoided: death, taxes, and protecting groups. Indeed, protecting groups mask functionality that would otherwise be compromised or interfere with a given reaction, making them a necessity in organic synthesis. In this chapter, for each protecting group showcased, only the most widely used methods for protection and cleavage are shown. Also, this section is not comprehensive and only addresses some of the most common blocking groups in organic synthesis. For a thorough review of protecting groups, the reader should consult the following references: (a) Wuts, P. G. M.; Greene, T. W.; Protective Groups in Organic Synthesis, 4th ed.; Wiley: Hoboken, NJ, 2007; (b) Kocienski, P. J. Protecting Groups, 3rd edition.; Thieme: Stuggart, 2004. In this section, the formation and cleavage of eight protecting groups for alcohols and phenols are presented: acetate; acetonides for diols; benzyl ether; para-methoxybenzyl (PMB) ether; methyl ether; methoxymethylene (MOM) ether; tert-butyldiphenylsilyl (TBDPS) silyl ether; and tetrahydropyran (THP). Acetate is a convenient protecting group for alcohols—easy on and easy off. Selective protection of a primary alcohol in the presence of a secondary alcohol can be achieved at low temperature. The drawback of this protecting group is its incompatibility with hydrolysis and reductive conditions.

ChemInform Abstract: Protecting Groups in Solid-Phase Organic Synthesis

ChemInform ◽  
2010 ◽  
Vol 33 (11) ◽  
pp. no-no
Author(s):  
David Orain ◽  
John Ellard ◽  
Mark Bradley
Keyword(s):  
Organic Synthesis ◽  
Solid Phase ◽  
Protecting Groups ◽  
Solid Phase Organic Synthesis

1,3-syn-Diaxial Repulsion of Typical Protecting Groups Used in Carbohydrate Chemistry in 3-O-Substituted Derivatives of Isopropyl d-Idopyranosides

2017 ◽  
Vol 82 (17) ◽  
pp. 8897-8908 ◽  
Author(s):  
Bozhena S. Komarova ◽  
Alexey G. Gerbst ◽  
Anastasiia M. Finogenova ◽  
Andrey S. Dmitrenok ◽  
Yury E. Tsvetkov ◽  
...  
Keyword(s):  
Protecting Groups ◽  
Carbohydrate Chemistry ◽  
Derivatives Of
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