Molecules 2005, 10(7), 772-782; doi:10.3390/10070772
Article

Regioselective Synthesis of Vinylic Derivatives of Common Monosccarides Through Their Activated Stannylene Acetal Intermediates

Received: 16 April 2004; in revised form: 4 November 2004 / Accepted: 6 November 2004 / Published: 31 August 2005
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: The regioselective C-2-O-acrylation and metacrylation of methyl 4,6-O-benzylidene-α-D-glucopyranoside and methyl 4,6-O-benzylidene-α-D-galactopyranosidethrough their corresponding organotin intermediates have been studied. Regioselectivitywas achived through the formation of a tin chelate of the 2,3-diols. Thus, methyl 4,6-O-benzylidene-α-D-glucopyranoside and methyl 4,6-O-benzylidene-α-D-galactopyranosidewere reacted with dibutylstannylene to give the corresponding dibutylstannylene acetalintermediates that were then reacted in a regioselective manner with acryloyl chloride ormetacryloyl chloride in the presence of triethylamine (TEA) or pyridine to give thevinylic type monomeric compounds. The monomeric products containing glucose andgalactose units from each reaction were separated by column chromatography using agradient of n-hexane and ethyl acetate as eluant. The structure of the obtained compoundswere confirmed using 1H-, 13C- and 2D NMR spectroscopy.
Keywords: Regioselectivity; monosaccharides; tin intermediates; acrylation and metacrylation
PDF Full-text Download PDF Full-Text [222 KB, uploaded 18 June 2014 19:26 CEST]

Export to BibTeX |
EndNote


MDPI and ACS Style

Namazi, H.; Sharifzadeh, R. Regioselective Synthesis of Vinylic Derivatives of Common Monosccarides Through Their Activated Stannylene Acetal Intermediates. Molecules 2005, 10, 772-782.

AMA Style

Namazi H, Sharifzadeh R. Regioselective Synthesis of Vinylic Derivatives of Common Monosccarides Through Their Activated Stannylene Acetal Intermediates. Molecules. 2005; 10(7):772-782.

Chicago/Turabian Style

Namazi, H.; Sharifzadeh, R. 2005. "Regioselective Synthesis of Vinylic Derivatives of Common Monosccarides Through Their Activated Stannylene Acetal Intermediates." Molecules 10, no. 7: 772-782.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert