Compositions and methods for sulfation of carbohydrates and peptides via electron-deficient aryl sulfate diesters
AssigneeThe Trustees of Boston College
InventorsJia Niu, Chao Liu, Cangjie Yang
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AssigneeThe Trustees of Boston College
InventorsJia Niu, Chao Liu, Cangjie Yang
Estimating the term…
In one aspect, the disclosure relates to a facile strategy to introduce electron-deficient aryl sulfate diesters to silylated hydroxyl groups of carbohydrates and amino acids, among other substrates, wherein selective hydrolysis and the removal of an electron-deficient aromatic group allows for the efficient generation of sulfated carbohydrates, peptides, and other compounds. The incorporation of electron-deficient aryl sulfate diesters in the early stage of the synthesis of glycans, peptides, and the like, disclosed herein avoids time-consuming protecting group manipulations, simplifies the purification of sulfated products, and improves the overall yield and efficiency. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.
A method for deprotecting an aryl-masked sulfate diester to form a sulfated product, the method comprising contacting the aryl-masked sulfate diester, which is generated by reacting a silylated substrate with an aryl fluorosulfate, in a solvent with a strong base, wherein a reactivity of the aryl-masked sulfate diester can be tuned by electronic properties of aryl substituents.
A method for deprotecting an aryl-masked sulfate diester to form a sulfated product, the method comprising a step of oxidative inserting a catalyst into an aromatic SP2 carbon-oxygen bond and reductive eliminating an arene.
Dependencies are inferred from the claim text.