A Scalable Approach to Obtaining Orthogonally Protected β-d-Idopyranosides

Abstract

A practical method to obtain orthogonally protected D-idopyranose from D-galactose has been developed, which is the first method to enable synthesis of the challenging β-D-idopyranoside linkage. The method relies on a key double inversion at O-2 and O-3 in an easily prepared D-galactose derivative, which proceeds regio- and stereoselectively through a 2,3-anhydrotalopyranoside; reaction using a selection of alkoxides affords exclusively the 3-O-alkylidopyranoside, which can be used to generate an orthogonally protected monosaccharide. The process is scalable and requires minimal purification, so it could be used to produce building blocks to aid in the synthesis of various β-idopyranose-containing oligosaccharide targets to further probe their biological functions.

Expressive Writing and Marital Satisfaction: A Writing Sample Analysis

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An efficient and scalable synthesis of 2,4-di-N-acetyl-l-altrose (l-2,4-Alt-diNAc)

“…These results are in sharp contrast with those obtained with conformationally restricted pyranosyl substrates that bear a fused 4,6-O-benzylidene ring: in those cases, excellent regio and stereoselectivity are normally achieved. [33][34][35][36][37][38] In our case, compound 26 is a non-rigid system that undergoes rapid conformational exchanges between the O H 5 and 5 H O conformations, especially at higher temperatures, giving the observed results.…”

Short Synthetic Route to Benzaldehyde‐Functionalized Idose and Talose Derivatives by Acetoxonium Ion Rearrangements

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