135681-59-3

Upstream product

• 74923-98-1 (R)-3,4-dihydroxybutanenitrile 
• 98-59-9 p-toluenesulfonyl chloride 
• 113826-06-5 (R)-glycidyl tosylate 

Downstream Products

• 135870-51-8 (R)-3-hydroxy-4-(p-toluenesulfonyloxy)butylamine hydrochloride 
• 121799-47-1 (R)-4-amino-3-hydroxybutyronitrile 
• 137487-59-3 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-2-cyano-1-(toluene-4-sulfonyloxymethyl)-ethyl ester 
• 137487-58-2 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-2-cyano-1-(toluene-4-sulfonyloxymethyl)-ethyl ester 

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.

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.