83527-35-9

Upstream product

• 74889-59-1 (DL)-2,2-dimethyl-4-(cyanomethyl)-1,3-dioxolane 
• 143-33-9 sodium cyanide 
• 96-24-2 3-monochloro-1,2-propanediol 
• 57090-45-6 (2R)-3-chloro-1,2-propanediol 
• 556-52-5 oxiranyl-methanol 
• 129097-92-3 3-bromo-5-(hydroxymethyl)-Δ²-isoxazoline 
• 151-50-8 potassium cyanide 

Downstream Products

• 137618-52-1 4-(benzyloxy)-3-hydroxybutanenitrile 
• 137618-66-7 2-benzyloxy-3-cyano propanol 
• 74889-61-5 (3RS)-3-hydroxy-4-p-toluenesulfonyloxybutyronitrile 

Relevant academic research and scientific papers

Lipase-catalyzed enantiomer separation of 3-hydroxy-4-(tosyloxy) butanenitrile: Synthesis of (R)-GABOB (=(3R)-4-amino-3-hydroxybutanoic acid) and (R)-carnitine hydrochloride (= (2R)-3-carboxy-2-hydroxy-N,N,N-trimethylpropan- 1-aminium chloride)

Enzymatic resolution of racemic 3-hydroxy-4-(tosyloxy)butanenitrile ((±)-5) by using various lipases in different solvents were studied. The obtained optically pure (3R)-3-(acetyloxy)-4-(tosyloxy)-butanenitrile ((R)-6), upon treatment with aqueous ammonia followed by cone. HCl solution, provided (R)-GABOB (=(3R)-4-amino-3-hydroxybutanoic acid; (R)-1). Similarly, reaction of (R)-6 with aqueous trimethylamine solution followed by cone. HCl solution provided (R)-carnitine hydrochloride (=(2R)-3-carboxy-2-hydroxy-N,N,N- trimethylpropan-1-aminium chloride; (R)-2·HCl) in an expeditious manner.

Highly regioselective conversion of epoxides to β-hydroxy nitriles with cyanide exchange resin

A simple and regioselective method is described for the efficient conversion of epoxides to β-hydroxy nitriles using Amberlite IRA-400 supported cyanide. The reactions occur in the absence of catalyst and furnish the corresponding β-hydroxy nitriles in high yields.

A new method for the preparation of β-hydroxy nitriles; Transformation of 3-bromo-2-isoxazolines to β-hydroxy nitriles by treatment of alkanethiolates

3-Bromo-2-isoxazolines are transformed to β-hydroxy nitriles in good yields by treatment with alkanethiolates under a very mild condition.

Method for preparing optically active 3,4-dihydroxy butyric acid derivatives

The present invention presents a method for preparation of S-3,4-dihydroxy butyronitrile expressed by the structural formula (II) STR1 characterized by causing R-3-chloro-1,2-propanediol expressed by the structural formula (I) STR2 to react with a cyanating agent. According to this invention, optically active 3,4-dihydroxy butyronitrile and 3,4-dihydroxy butyric acid derivatives may be manufactured economically and efficiently.

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.