157668-56-9

Upstream product

• 220871-52-3 1(R,S)-<1'-(S)-<(tert-butyloxycarbonyl)amino>-2-phenylethyl>oxirane 
• 497-19-8 sodium carbonate 
• 169057-29-8 (R)-1-(oxiran-2-yl)-2-phenylethanone 
• 98760-08-8 (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester 
• 144-55-8 sodium hydrogencarbonate 
• 77-92-9 citric acid 

Downstream Products

• 1236608-47-1 C₁₂H₁₅NO₅S 

Relevant academic research and scientific papers

Synthesis and antimalarial activity of thioetherhydroxyethylsulfonamides, potential aspartyl protease inhibitors, Part 3

A series of novel thioetherhydroxyethylsulfonamide derivatives has been synthesized from the coupling of intermediates 3-amino-4-phenyl-1- thioetherazine-butan-2-oles 6,7 with arenesulfonyl chlorides in good yields. Characterizations of products were achieved by NMR techniques and specifically for compound 8e by X-ray crystallography. Preliminary results of antimalarial activity in vitro against the Plasmodium falciparum W2 clone (chloroquine resistant and mefloquine sensitive) showed moderate activity for hydroxyethylsulfonamide 8f. In addition, none of the compounds tested showed cytotoxicity at high concentration tested against HepG2 and BGM cell lines.

Production method of beta-amino-alpha-hydroxycarboxylic acid

The present invention provides a production method of an optically active β-amino-α-hydroxycarboxylic acid, which includes the following steps (a)-(c): (a) treating an optically active N-carbamate protected β-amino epoxide with an acid to give an optically active 5-hydroxymethyl-2-oxazolidinone; (b) oxidizing the resulting compound in the presence of 2,2,6,6-tetramethyl-1-piperidinyloxy and hypochlorite to give an optically active 4-benzyl-2-oxo-5-oxazolidinecarboxylic acid; and (c) treating the 4-benzyl-2-oxo-5-oxazolidinecarboxylic acid with a base, and a production method of an optically active N-carbamate protected β-amino-α-hydroxycarboxylic acid which includes protection of the amino group with a carbamate type protecting group. The industrial production method of the present invention can produce these compounds efficiently.

Method for producing epoxide crystal

The invention relates to a method for industrially producing highly pure (2R, 3S)- or (2S, 3R)-N-carbamate-protected β-aminoepoxide (crystal) or (2R, 3S)- or (2S, 3R)-N-carbamate-protected β-aminoalcohol. The method for producing N-carbamate-protected β-aminoepoxide crystal, includes one or more of the following steps (a) to (d): (a) dissolving (2R, 3S)- or (2S, 3R)-N-carbamate-protected β-aminoalcohol containing at least the diastereomer as an impurity in a solvent including at least one or more selected from aromatic hydrocarbon solvent, saturated hydrocarbon solvent, aqueous mixture solvent, acetone and 2-propanol, to remove insoluble matters; (b) treating the (2R, 3S)- or (2S, 3R)-N-carbamate-protected β-aminoalcohol with a base, thereby converting the N-carbamate-protected β-aminoalcohol to (2R, 3S)- or (2S, 3R)-N-carbamate-protected β-aminoepoxide; (c) treating the (2R, 3S)- or (2S, 3R)-N-carbamate-protected β-aminoepoxide containing at least the diastereomer as an impurity with an acid, thereby converting the diastereomer as an impurity to (4S, 5R) or (4R, 5S) oxazolidin-2-one derivative, and optionally separating and removing the resulting oxazolidin-2-one derivative in water or an aqueous mixture solvent; and (d) crystallizing the (2R, 3S)- or (2S, 3R)-N-carbamate-protected β-aminoepoxide in a mixture solvent of water and water-miscible organic solvent. By the methods of the present invention, highly pure (2R, 3S)- or (2S, 3R)-N-carbamate-protected β-aminoepoxide or (2R, 3S) or (2S, 3R)-N-carbamate-protected β-aminoalcohol can be efficiently produced.

A General Stereocontrolled Synthesis of Hydroxyethylene Dipeptide Isosteres

Hydroxyethylene dipeptide isosteres were synthesized by stereocontrolled hydroboration of homoallylic alcohols derived from syn protected aminoepoxides followed by chemoselective oxidation of the resulting primary alcohols.

Stereoselective synthesis of protected amino alkyl epoxides

The mechanism of epoxidation of chiral allyl amines has been investigated. The intrinsic stereoselectivity for epoxidation is shown to be approximately 5:1 and is independent of the nitrogen substituent. However, the nature of the N-protecting group influences the stability of the undesired epoxide to the acidic media, with the minor diastereomer undergoing preferential decomposition. Conditions are reported for the highly stereoselective synthesis of epoxide 9R, an important building block in the synthesis of several enzyme inhibitors.