Synthesis of alpha-glucuronic acid and amide derivatives in the presence of a participating 2-acyl protecting group

Organic Letters
Manuela Tosin, Paul V Murphy

Abstract

[reaction: see text] Participating acyl groups located at C-2 in glucosyl and related donors generally promote formation of 1,2-trans-glycosides. Reactions of some glucuronic acid donors with TMSN(3)/SnCl(4) or ROH/SnCl(4) gave only the 1,2-cis-glycoside. The stereoselectivity is consistent with participation of the C-6 group. The methodology was used for the synthesis of a Kdn2en mimetic with the alpha-configuration.

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Citations

May 5, 2007·Carbohydrate Research·Christina LoukouPaul V Murphy
Aug 14, 2009·Organic & Biomolecular Chemistry·Jason R McCarthyRalph Weissleder
Sep 17, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Wayne PilgrimPaul V Murphy
Jan 23, 2016·Organic Letters·Anthony W McDonaghPaul V Murphy
Jun 6, 2006·Advances in Carbohydrate Chemistry and Biochemistry·Z Györgydeák, Joachim Thiem
May 19, 2017·Organic & Biomolecular Chemistry·Nuno M XavierM Conceição Oliveira
Oct 11, 2011·Archiv der Pharmazie·Ahmed O H El-NezhawyTarek B A El-Naggar
Mar 5, 2014·Chemistry : a European Journal·Mark FarrellPaul V Murphy
Apr 7, 2018·Beilstein Journal of Organic Chemistry·Jayashree RajputMadhuri Vangala
Feb 20, 2004·Chemical Communications : Chem Comm·Manuela TosinPaul V Murphy
Jun 10, 2009·Chembiochem : a European Journal of Chemical Biology·Manuela TosinJonathan B Spencer

Related Concepts

Amides
Glucuronic Acid, 6-(14)C-labeled, (D)-isomer

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