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Synthesis of Methyl 2,3,5-Tri-O-benzoyl-α[alpha]-d-arabinofuranoside in the Organic Laboratory
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Abstract
We report an organic chemistry laboratory experiment in which methyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside is synthesized. The product is obtained in two steps from commercially available D-arabinose, via Fischer glycosylation and benzoylation. The product is easily purified by crystallization. The primary purpose in implementing this experiment was to give students additional exposure to carbohydrate chemistry. In addition, the experiment provides an opportunity to discuss a number of other topics including kinetic vs thermodynamic control of reactions, mutarotation, the synthesis of esters, recrystallization, the separation of diastereomers, and optical activity. It is also possible to incorporate 2-D NMR spectroscopy into this experiment.
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Keywords (Audience):
Upper-Division UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
CarbohydratesCiting Articles
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This article has been cited by 11 ACS Journal articles (5 most recent appear below).
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Erkki Nurminen , Päivi Poijärvi , Katja Koskua and Jari HovinenJournal of Chemical Education2007 84 (9), 1480Treatment of d-fructose with methanol in the presence of acid as a catalyst gives a mixture of methyl-β-d-fructopyranoside, methyl-α-D-fructofuranoside, and methyl-β-d-fructofuranoside, which were separated on an ion exchange column and characterized ...
Synthesis of the Docosanasaccharide Arabinan Domain of Mycobacterial Arabinogalactan and a Proposed Octadecasaccharide Biosynthetic Precursor
Maju Joe, Yu Bai, Ruel C. Nacario, and Todd L. LowaryJournal of the American Chemical Society2007 129 (32), 9885-9901Synthesis of the Docosanasaccharide Arabinan Domain of Mycobacterial Arabinogalactan and a Proposed Octadecasaccharide Biosynthetic Precursor
Maju Joe, Yu Bai, Ruel C. Nacario, and Todd L. LowaryJournal of the American Chemical Society2007 129 (32), 9885-9901Two major components of the cell wall in mycobacteria, including Mycobacterium tuberculosis, the causative agent of tuberculosis (TB), are polysaccharides containing arabinofuranose residues. In one of these polysaccharides, arabinogalactan, this arabinan ...
On the Use of 3,5-O-Benzylidene and 3,5-O-(Di-tert-butylsilylene)-2-O-benzylarabinothiofuranosides and Their Sulfoxides as Glycosyl Donors for the Synthesis of β-Arabinofuranosides: Importance of the Activation Method
David Crich, Christian Marcus Pedersen, Albert A. Bowers, and Donald J. WinkThe Journal of Organic Chemistry2007 72 (5), 1553-1565On the Use of 3,5-O-Benzylidene and 3,5-O-(Di-tert-butylsilylene)-2-O-benzylarabinothiofuranosides and Their Sulfoxides as Glycosyl Donors for the Synthesis of β-Arabinofuranosides: Importance of the Activation Method
David Crich, Christian Marcus Pedersen, Albert A. Bowers, and Donald J. WinkThe Journal of Organic Chemistry2007 72 (5), 1553-1565A 2-O-benzyl-3,5-O-benzylidene-α-d-thioarabinofuranoside was obtained by reaction of the corresponding diol with α,α-dibromotoluene under basic conditions. On activation with 1-benzenesulfinyl piperidine, or diphenyl sulfoxide, and ...
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- Received: August 03, 2009
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