Chiral Alcohols

We offer a wide range of chiral alcohols to meet their ever-growing demand. These useful reagents may serve both as starting materials in the synthesis of single-stereoisomer drugs or intermediates, or as powerful resolving agents.

2-Hexanol

(R)-(–)-2-Hexanol and (S)-(+)-2-hexanol were used in the preparation of some key intermediates for model studies in the total synthesis of antivirally active glycolipid cycloviracin B₁ (Scheme 1). By comparing the NMR chemical shifts of the synthesized model compounds with the ones of the isolated natural product, configurations of four previously unassigned stereocenters of cycloviracin B₁ could be elucidated.

Scheme 1. Hexanol

2-Heptanol

The (R)-enantiomer of 2-heptanol was used by Kondo et al. in resolving the diastereoisomeric mixture of a key intermediate in the synthesis of 1-(2-chloro-4-pyrrolidin-1-ylbenzoyl)-2,3,4,5-tetrahydro-1H-1-benzdiazepine, known to be a strong vasopressin V₂ receptor agonist, which helps to maintain normal plasma osmolality, blood volume, and blood pressure (Scheme 2). A nonpeptidic V₂ agonist may find use in the treatment of diabetes insipidus and nocturnal enuresis.

Scheme 2. Heptanol

References

1. Fürstner A, Albert M, Mlynarski J, Matheu M, DeClercq E. 2003. Structure Assignment, Total Synthesis, and Antiviral Evaluation of Cycloviracin B1. J. Am. Chem. Soc.. 125(43):13132-13142. https://doi.org/10.1021/ja036521e

2. Kondo K, Kan K, Tanada Y, Bando M, Shinohara T, Kurimura M, Ogawa H, Nakamura S, Hirano T, Yamamura Y, et al. 2002. Characterization of Orally Active Nonpeptide Vasopressin V2Receptor Agonist. Synthesis and Biological Evaluation of Both the (5R)- and (5S)-Enantioisomers of 2-[1-(2-Chloro-4-pyrrolidin-1-yl-benzoyl)-2,3,4,5-tetrahydro-1H-1-benzazepin- 5-yl]-N-isopropylacetamide. J. Med. Chem.. 45(17):3805-3808. https://doi.org/10.1021/jm020133q