Skip to Content
Merck
  • Synthesis of novel polyhydroxylated pyrrolidine-triazole/-isoxazole hybrid molecules.

Synthesis of novel polyhydroxylated pyrrolidine-triazole/-isoxazole hybrid molecules.

Organic & biomolecular chemistry (2014-12-20)
Cheng-Kun Lin, Li-Wei Cheng, Huang-Yi Li, Wen-Yi Yun, Wei-Chieh Cheng
ABSTRACT

A straightforward synthesis of novel, 2-heterocyclyl polyhydroxylated pyrrolidines is described. Stereocontrolled additions of nucleophiles to cyclic nitrones generated the corresponding 2,3-trans adducts, allowing the synthesis of the corresponding pyrrolidines via key intermediates bearing an alkyne and a nitrile oxide. Three hybrid systems, including a pyrrolidine with two isoxazoles and one triazole, are efficiently prepared via 1,3-dipolar cycloaddition. Biological testing of the product alkaloids showed that subtle structural variations have drastic effects on their inhibitory activities against glucosidases.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Methanol-d4, ≥99.8 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Methanol-d4, ≥99.8 atom % D, contains 1 % (v/v) TMS
Sigma-Aldrich
Methanol-d4, "100%", 99.96 atom % D
Sigma-Aldrich
Methanol-d4, ≥99.8 atom % D, contains 0.05 % (v/v) TMS
Sigma-Aldrich
Methanol-d4, anhydrous, ≥99.8 atom % D
Sigma-Aldrich
Methanol-d4, ≥99.8 atom % D, contains 0.1 % (v/v) TMS
Sigma-Aldrich
Methanol-d4, 99 atom % D
Sigma-Aldrich
Methanol-d4, ≥99.8 atom % D
Sigma-Aldrich
Methanol-d4, "100%", ≥99.96 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
β-Glucosidase from almonds, lyophilized powder, ≥2 units/mg solid
Sigma-Aldrich
Methanol-d4, ≥99.8 atom % D
Sigma-Aldrich
α-Glucosidase from Bacillus stearothermophilus, lyophilized powder, ≥50 units/mg protein