Publication

C-glycosides and C-disaccharide precursors through carbonylative Stille coupling reactions

Pierre Vogel
1997
Journal Articles

Abstract

Under CO atmosphere and in the presence of Pd-2(dba)(3) and Ph(3)As a suitably protected 1-stannylglucal derivative could be carbonylated and coupled to 5-bromo-7-oxabicyclo[2.2.1]hept-5-en-2-yl derivatives. The carbonylative Stille coupling was also successful between 1-iodoglucals and tributyl(vinyl)stannane or tributyl(fur-2-yl)stannane. A cross-conjugated dienone was also obtained through coupling of a 1-stannylglucal with a 1-iodoglucal derivative. (C) 1997, Published by Elsevier Science Ltd. All rights reserved.

Official source

https://infoscience.epfl.ch/entities/publication/d0ac4166-2834-47fd-ba4e-260653e305aa

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Pierre Vogel
1997
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/d0ac4166-2834-47fd-ba4e-260653e305aa

About this result

Related concepts (17)

Stille reaction

The Stille reaction is a chemical reaction widely used in organic synthesis. The reaction involves the coupling of two organic groups, one of which is carried as an organotin compound (also known as organostannanes). A variety of organic electrophiles provide the other coupling partner. The Stille reaction is one of many palladium-catalyzed coupling reactions. Allyl, alkenyl, aryl, benzyl,acyl halides (Cl, Br, I), pseudohalides (OTf, OPO(OR)2), OAc The R1 group attached to the trialkyltin is normally sp2-hybridized, including vinyl, and aryl groups.

Glycoside

In chemistry, a glycoside ˈɡlaɪkəsaɪd is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of Heliconius butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators.

Glycosidic bond

A glycosidic bond or glycosidic linkage is a type of ether bond that joins a carbohydrate (sugar) molecule to another group, which may or may not be another carbohydrate. A glycosidic bond is formed between the hemiacetal or hemiketal group of a saccharide (or a molecule derived from a saccharide) and the hydroxyl group of some compound such as an alcohol. A substance containing a glycosidic bond is a glycoside.

Related publications (4)

C-glycosides and C-disaccharide precursors through carbonylative Stille coupling reactions

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Heterogeneous coupling by virtual control methods

Selective immobilization of active 6-O-Alkylguanine DNA alkyltransferase for its determination by transferring a coupling group to the enzyme from a 6-O-Alkylguanine derivative

Highly cis-selective Wittig reactions employing a-heterosubstituted ylides