95586-53-1

Usage

Uses

Used in Pharmaceutical Industry:
(2R)-2-(tetrahydro-2H-pyran-2-yloxy)propanoic acid is used as a synthetic intermediate for the preparation of various pharmaceutical compounds. Its unique structural features allow it to serve as a building block in the synthesis of complex organic molecules, particularly those with biological activity.
Used in Organic Synthesis:
(2R)-2-(tetrahydro-2H-pyran-2-yloxy)propanoic acid is used as a versatile synthetic building block for the preparation of a wide range of organic compounds. Its ability to participate in various chemical reactions makes it a valuable asset in the synthesis of target molecules with specific properties and functions.
Used in Solid Phase Synthesis:
(2R)-2-(tetrahydro-2H-pyran-2-yloxy)propanoic acid is used as a key component in the solid phase synthesis of lactic acid oligomers, depsides, and depsipeptides. This approach allows for the efficient and controlled assembly of complex molecules, which can be crucial for the development of new drugs and bioactive compounds.

Upstream product

• 124508-74-3 (2R)-2-(tetrahydro-2H-pyran-2-yloxy)propanoic acid methyl ester 

Relevant academic research and scientific papers

Solid-phase synthesis of enantio-controlled lactic acid oligomers

A synthetic method for lactic acid oligomers via solid-phase synthesis under mild reaction conditions with up to 99% yield is presented. The fine control of the chirality on each lactic acid unit of the oligomers was easily achieved by the substitution of (R)-THP-protected lactic acid (R)-2 by (S)-2 without alternating the procedure. The overall synthesis of the trimer and tetramer was completed in one and two days, respectively. Intramolecular cyclizations of enantio-controlled lactic acids were also attempted through the Yamaguchi macrolactonization or the Mitsunobu reaction. However, we were unable to isolate single cyclic oligomers but always obtained a mixture of cyclic oligomers.

Anthelmintic PF1022A: Stepwise solid-phase synthesis of a cyclodepsipeptide containing N-methyl amino acids

Cyclodepsipeptides of the enniation-, PF1022-, and verticilide-family represent a diverse class of highly interesting natural products with respect to their manifold biological activities. However, until now no stepwise solid-phase synthesis has been accomplished due to the difficult combination of N-methyl amino acids and hydroxycarboxylic acids. We report here the first stepwise solid-phase synthesis of the anthelmintic cyclooctadepsipeptide PF1022A based on an Fmoc/THP-ether protecting group strategy on Wang-resin. The standard conditions of our synthesis allow an unproblematic adaption to an automated peptide synthesizer.