74923-98-1

Upstream product

• 74923-97-0 (R)-2,2-dimethyl-4-(cyanomethyl)-1,3-dioxolane 
• 105-33-9 4-chloro-3-hydroxybutyronitrile 
• 890050-56-3 (R)-3-Hydroxy-4-trityloxy-butyronitrile 
• 852805-30-2 (R)-3-hydroxy-4-(4-methoxyphenoxy)butanenitrile 

Downstream Products

• 135681-59-3 (R)-3-hydroxy-4-(p-toluenesulfonyloxy)butyronitrile 

Relevant academic research and scientific papers

Lipase-mediated resolution of 3-hydroxy-4-trityloxybutanenitrile: synthesis of 2-amino alcohols, oxazolidinones and GABOB

Lipase-mediated kinetic resolution of 3-hydroxy-4-trityloxybutanenitrile gave the (S)-alcohol and (R)-acetate in good yields and high enantioselectivities. The resolution using Pseudomonas cepacia lipase (Burkholderia cepacia) immobilized on modified cera

New chemoenzymatic pathway for β-adrenergic blocking agents

The lipase mediated kinetic resolution of pharmaceutically important β-hydroxy nitriles is described in high enantiomeric excesses and good yields. Some of the chiral β-hydroxy nitriles have been employed in the synthesis of β-adrenergic blocking agents such as propranolol, alprenolol and moprolol. This protocol has also been extended for the enantiopure preparation of 5-(4-tosyloxymethyl)-1,3-oxazolidine-2-one and 3-hydroxy-4-tosyloxybutanenitrile, chiral intermediates of high synthetic value.

Production of (S)-4-chloro-3-hydroxybutyronitrile using microbial resolution

A new production procedure of (S)-4-chloro-3-hydroxybutyronitrile was developed using microbial resolution. The resting cells of Pseudomonas sp. OS-K-29 preferentially converted (R)-4-chloro-3-hydroxybutyronitrile to the corresponding 1,2-diol by the dehalogenating activity so that (S)-4-chloro-3-hydroxybutyronitrile (94.5%ee) was obtained from the racemate in 40% yield at the microbial resolution step.

Total Synthesis of (R)-Glycerol Acetonide and the Antiepileptic and Hypotensive Drug (-)-γ-Amino-β-hydroxybutyric Acid (GABOB): Use of Vitamin C as a Chiral Starting Material

Ascorbic acid (Vitamin C) (9) is shown to be a useful, inexpensive chiral starting material for natural products synthesis.It is converted in high yield via two synthetic operations into (R)-glycerol acetonide (7), the more inaccessible enantiomer of glycerol acetonide.Since D-(R)-glyceraldehyde acetonide (4) and the corresponding alcohol 1 have been used in many total syntheses of a wide variety of compounds, the ready availability of the opposite enantiomers L-(S)-glyceraldehyde acetonide (6) and glycerol (7) should be of greate value.As one indication of this potential synthetic utility, the hypotensive, antiepileptic compound (R)-(-)-γ-amino-β-hydroxybutyric acid (GABOB) (8) has been synthesized from ascorbic acid (9) via nine steps in 10percent overall yield.As further evidence of the importance of these synthesis, several useful intermediates for the preparation of the highly active hypotensive agents, the aryloxypropanolamines (5), were prepared from Vitamin C.