AI Article Synopsis
- The axial 2-hydroxyl group of methyl and allyl 3-O-benzyl-alpha-L-rhamnopyranosides can be selectively acylated using acyl chloride and silver(I) oxide, yielding 56-78%.
- This method was effective in synthesizing a protected tetrasaccharide fragment that is part of the triterpene saponins called gleditsiosides C and D.
- The process highlights a useful approach in organic chemistry for modifying carbohydrate structures for further study or application.
Article Abstract
The axial 2-hydroxyl group of methyl and allyl 3-O-benzyl-alpha-L-rhamnopyranosides was selectively acylated in 56-78% yields by reaction with 1.1 equiv of acyl chloride in the presence of 1.5 equiv of silver(I) oxide. Use of the method permitted a convenient synthesis of a protected tetrasaccharide fragment of triterpene saponins gleditsiosides C and D.
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| http://dx.doi.org/10.1016/j.carres.2007.03.001 | DOI Listing |
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