One step stereoselective synthesis of oxazoline-fused saccharides and their conversion into the corresponding 1,2-<i>cis</i> glycosylamines bearing various protected groups

Trifluoromethanesulfonic anhydride (Tf 2 O) exhibits excellent reactivity as an electrophile, serving as a highly versatile reagent in diverse chemical transformations. Herein, we report an operationally simple, efficient, unique, and practical one-step strategy for synthesizing diverse valuable structures bearing furo[3,2-b]furans core leveraging Tf 2 O's promoted reactivity of nitriles with diacetonide protected furanose. Furthermore, we demonstrate the potential of furo[3,2-b]furan as a precursor for complex structures through 1,3-dipolar cycloaddition.

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Triflic Anhydride-Mediated Unprecedented Reactivities of Diacetonide Endoglucofuranose and Ribose Tetracetate: Direct Access to γ-Butenolides and Oxazoles

Sakander,

Dar,

Ahmed

2024

J. Org. Chem.

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Herein, we present two unprecedented reactions for the synthesis of γ-butenolides and oxazoles, leveraging Tf 2 O's promoted reactivity of nitriles with diacetonide endoglucofuranose and 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose. This method is highly efficient and straightforward and employs a one-step, metal-free protocol. It is effective with both aromatic and aliphatic nitriles and demonstrates a broad substrate scope. Our approach provides a versatile and practical pathway for the synthesis of structurally diverse compounds, significantly expanding the utility of Tf 2 O in synthetic chemistry.

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One step stereoselective synthesis of oxazoline-fused saccharides and their conversion into the corresponding 1,2-cis glycosylamines bearing various protected groups

Abstract: Oxazolinoses, which can be converted into 1,2-cis glycosylamines and allowed the access to schisandrin derivatives, are prepared concisely from peracetylated saccharides and benzonitriles under acidic conditions with stoichiometric amounts of water.

Cited by 3 publications

References 28 publications

Five-membered ring systems with O and N atoms

Five-membered ring systems with O and N atoms

Triflic Anhydride-Mediated Approach to Furo[3,2-b]furans from Diacetonide Protected Furanoses

Triflic Anhydride-Mediated Unprecedented Reactivities of Diacetonide Endoglucofuranose and Ribose Tetracetate: Direct Access to γ-Butenolides and Oxazoles

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