118712-64-4

Upstream product

• 108-05-4 vinyl acetate 
• 74889-61-5 (3RS)-3-hydroxy-4-p-toluenesulfonyloxybutyronitrile 
• 126577-60-4 (3S)-3,4-dihydroxybutyronitrile 
• 98-59-9 p-toluenesulfonyl chloride 
• 113826-06-5 (R)-glycidyl tosylate 
• 5804-85-3 diethylaluminium cyanide 

Downstream Products

• 135870-54-1 (S)-3-hydroxy-4-(p toluenesulfonyloxy)butylamine hydrochloride 
• 135590-85-1 isobutyl (3S)-3-hydroxy-4-(p-toluenesulfonyloxy)butyrate 
• 100243-39-8 3-hydroxypyrrolidine 

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.

Process for the production of 3,4-epoxybutyrate and intermediate therefor

A 3,4-epoxybutyrate of the formula: STR1 wherein R1 is an alkyl or aralkyl group is efficiently prepared by a process comprising steps of: (a) reacting 3,4-dihydroxybutyronitrile of the formula: STR2 with a sulfonyl chloride of the formula: Rs

Ring-opening of glycidyl derivatives by silanes mediated by Ti(O-i-Pr)4 or Al(O-i-Pr)3: Access to versatile C3 building blocks

Ring-opening of chiral glycidol or glycidyl tosylate by Me3SiN3 or Me3SiCN catalyzed by Ti(O-i-Pr)4 or Al(O-i-Pr)3 occurred in a regiospecific manner and with very high stereoselectivity, leading to new trifunctionalized chiral building blocks. The enantiomeric excess of the ring-opened products was 90-95%, as determined by 1H NMR of the Mosher ester derivatives, indicating that there was no significant loss of optical purity during the ring-opening. This methodology was applied for the one-pot synthesis of (R)-1-azido-3-naphthyloxy-2-hydroxypropane in 94% ee, a precursor of analogs of propranolol.

Arenesulfonate Derivatives of Homochiral Glycidol: Versatile Chiral Building Blocks for Organic Synthesis

The preparation of a series of crystalline arenesulfonate derivatives of enantiomerically enriched glycidol is described.The enhancement of optical purity by recrystallization was particularly successful for two of these derivatives, glycidyl tosylate and glycidyl 3-nitrobenzenesulfonate, which were obtained in 97 percent ee and 99 percent ee, respectively.Very high regioselectivity was observed in the reactions of these compounds with a variety of nucleophiles, including aryl oxides, Et2AlCN, organometallic reagents, and BH3-NaBH4.The application of this methodology to the synthesis of homochiral β-adrenergic blocking agents and homochiral terminal epoxides is discussed.