83023-80-7

Upstream product

• 108-98-5 thiophenol 
• 82044-23-3 R-oxiranecarboxylic acid potassium salt 
• 111248-06-7 methyl 2-hydroxy-3-(phenylthio)-propionate 
• 111248-38-5 phenylthioacetaldehyde cyanohydrin acetate 
• 111248-41-0 2-(1-pyrrolidinyl)-3-phenylthiopropionitrile 
• 51877-54-4 potassium oxirane-2-carboxylate 

Downstream Products

• 128677-43-0 (2S,5S)-2-tert-Butyl-5-phenylsulfanylmethyl-[1,3]dioxolan-4-one 
• 128677-43-0 (2S,5R)-2-tert-Butyl-5-phenylsulfanylmethyl-[1,3]dioxolan-4-one 
• 111248-06-7 methyl β-(thiophenoxy)lactate 
• 128677-43-0 (2S,5S)-2-tert-butyl-5-<(phenylthio)methyl>-1,3-dioxolan-4-one 
• 140850-04-0 (2R,5S)-2-tert-butyl-5-<(phenylthio)methyl>-1,3-dioxolan-4-one 
• 128677-44-1 (2S,5S)-2-cyclohexyl-5-<(phenylthio)methyl>-1,3-dioxolan-4-one 
• 140850-78-8 (2R,5S)-2-cyclohexyl-5-<(phenylthio)methyl>-1,3-dioxolan-4-one 
• 200571-98-8 (2R,5S)-2-[(3E,5Z)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-methyl-hepta-3,5-dienyl]-5-phenylsulfanylmethyl-[1,3]dioxolan-4-one 
• 82044-25-5 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-methoxycarbonyl-2-phenylsulfanyl-ethyl ester 
• 82971-70-8 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-methoxycarbonyl-2-phenylsulfanyl-ethyl ester 
• 1370639-66-9 C₁₅H₁₈O₃S 
• 140663-05-4 (2S,5R)-5-Benzenesulfonylmethyl-2-cyclohexyl-[1,3]dioxolan-4-one 
• 128677-44-1 (2S,5S)-2-Cyclohexyl-5-phenylsulfanylmethyl-[1,3]dioxolan-4-one 
• 128677-44-1 (2S,5R)-2-Cyclohexyl-5-phenylsulfanylmethyl-[1,3]dioxolan-4-one 

Relevant academic research and scientific papers

Enantioselective, chromatography-free synthesis of β3-Amino acids with natural and unnatural side chains

β3-Amino acids are key components of some pharmaceuticals, excellent surrogates for metabolically labile α-amino acids, and building blocks for chiral heterocycles. Unfortunately they are not easily accessible in enantiomerically pure form, especially when possessing unnatural side chains. A flexible, chromatography-free process for the synthesis of enantiopure β3-amino acids possessing natural and unnatural side chains is described. The procedure uses inexpensive starting materials and reagents and offers a good alternative to the hazardous and expensive Arndt-Eistert homologation of enantiopure α-amino acids. Its utility has been demonstrated with the preparative scale synthesis of two valuable β3-amino acids possessing unnatural side chains.

Enantioselective Synthesis of 2-Alkyl-5-methylene-1,3-dioxolan-4-ones and Exo-Selective Diels-Alder Reactions with Cyclopentadiene

Highly stereoselective syntheses of chiral dienophiles (R)-1 and (R)-2 are described.Diazotization of L-serine in the presence of HCl and then treatment of the resulting β-hydroxy-α-chloropropionic acid (S)-7 with KOH provides potassium glycidate ((R)-8) in good yield and high enantiomeric purity.Treatment of (R)-8 with PhSH in MeOH then provides α-hydroxy acid (S)-10 that can be purified by recrystallization.Condensation of (S)-10 with either pivalaldehyde or cyclohexanecarboxaldehyde followed by oxidation to the sulfone and DBU-promoted elimination of benzenesulfinic acid then provides dienophiles (R)-1 and (R)-2, respectively.Highly exo-selective Diels-Alder reactions of (R)-1 and (R)-2 with cyclopentadiene are also described.The major cycloadduct (-)-15 (94percent of total) from the Diels-Alder reaction of 1 was shown to have an enantiomeric purity of 99percent ee.This figure defines the lower limit of enantiomeric purity of (R)-1.The diastereofacial selectivity of the Diels-Alder reactions of 1 in the exo manifold (50:1) is greater than that of 2 (20:1), as would be expected on the basis of the different steric requirements of the tert-butyl and cyclohexyl substituents of the two reagents.Consequently, dienophile 1 is the preferred reagent for complex synthetic applications, either as a chiral ketene equivalent or in contexts in which the α-hydroxy acid funtionality will be preserved in the ultimate synthetic target.Finally, the possible role of dipole effects on the exo selectivity of the Diels-Alder reactions of these and related dienophiles are briefly discussed.

Synthesis and Diels-Alder reactions of 2-alkyl-5-methylene-1,3-dioxolan-4-ones and 2-alkyl-3-acyl-5-methylene-1,3-oxazolidin-4-ones: Highly exo and diastereoface selective chiral ketene equivalents

Chiral dienophiles 1-3 undergo highly exo and diastereoface selective Diels-Alder reactions. The Diels-Alder reactions of 3 are also highly exo selective under Lewis acid catalyzed conditions.

A Formylcarbonium Ion Synthon. Synthesis of 3-Thio-Substituted 2-Amino Acids and Thio-Substituted Enamines from 2-Acyloxyacrylonitriles

The utilization of 2-acyloxy-3-phenylthiopropionitriles (2) which were prepared by the Michael addition of thiophenol to 2-acyloxyacrylonitriles (CH2=C(CN)OCOR), as a formylcarbonium ion synthon, was demonstrated by the transformation of 2 into S-phenylcysteine and 2-phenylthio enamines.

Laboratory-Scale Enzymatic/Chemical Syntheses of D- and L-β-Chlorolactic Acid and D- and L-Potassium Glycidate

This paper describes preparations of D- (and L-) chlorolactic acids having enantiomeric excesses greater than 97percent by D- (and L-) lactate dehydrogenase catalyzed reduction of chloropyruvic acid with NADH.In syntheses carried out on 0.1-0.5 mol scales