212896-12-3

Upstream product

• 17407-55-5 (S)-2-Hydroxy-3-methylbutanoic acid 
• 111199-07-6 (S)-2-hydroxy-3,N,N-trimethylbutanamide 
• 100-58-3 phenylmagnesium bromide 
• 97551-20-7 S-(+)-1-phenyl-2-hydroxy-3-methylbutanone 
• 736123-29-8 Amino-acetic acid (S)-1-benzoyl-2-methyl-propyl ester 
• 212896-13-4 (1S)-1-benzoyl-2-(tert-butoxycarbonylamino)-2-methylpropyl ethanoate 

Downstream Products

• 212896-14-5 (6S)-3-[(Z)-ethylidene]-6-isopropyl-5-phenyl-3,6-dihydro-2H-1,4-oxazin-2-one 
• 212896-17-8 (6S)-3-[(Z)-2,2-dimethylpropylidene]-6-isopropyl-5-phenyl-3,6-dihydro-2H-1,4-oxazin-2-one 
• 335164-05-1 (5R,6S)-6-isopropyl-5-phenylmorpholin-2-one 
• 278175-34-1 (1S,2R,4S,6'S)-bicyclo[2.2.1]hept-5-en-2-spiro{3[6'-isopropyl-5'-phenyl-3',6'-dihydro-2'H-1',4'-oxazin-2'-one]} 
• 278175-37-4 (3S,5R,6S)-3-isobutyl-6-isopropyl-4-methyl-5-phenyltetrahydro-2H-1,4-oxazin-2-one 
• 278175-32-9 (3S,5R,6S)-3-ethyl-6-isopropyl-4-methyl-5-phenyltetrahydro-2H-1,4-oxazin-2-one 
• 212896-20-3 (1R,3S,6S)-1-ethyl-6-isopropyl-7-phenyl-5-oxa-8-azaspiro[2.5]oct-7-en-4-one 

Relevant academic research and scientific papers

Synthesis of Chiral Alkenyl Cyclopropane Amino Acids for Incorporation into Stapled Peptides

α,α′-Disubstituted amino acids serve as important non-proteinogenic amino acids in the construction of stabilized helical peptides. To expand the repertoire of α,α′-disubstituted amino acids, chiral alkenyl-containing cyclopropane amino acids were synthes

BUILDING BLOCKS FOR STAPLED PEPTIDES

This invention relates to a method for producing an alkenyl 1 -aminocyclopropane-1 -carboxylic acid of Formula I wherein R1 is a protecting group, n is an integer between 1 and 10, and A and B are chiral centres such that when A is S, B is R an

New Chiral Didehydroamino Acid Derivatives from a Cyclic Glycine Template with 3,6-Dihydro-2H-1,4-oxazin-2-one Structure: Applications to the Asymmetric Synthesis of Nonproteinogenic α-Amino Acids

New chiral (Z)-α,β-didehydroamino acid (DDAA) derivatives with 3,5-dihydro-2H-1,4-oxazin-2-one structure 11a-f have been stereoselectively prepared after condensation of chiral glycine equivalent 7 with aldehydes in the presence of K2CO3 under mild solid-liquid phase-transfer catalysis reaction conditions. These new systems have been used in diastereoselective cyclopropanation reactions using Corey's ylide for the asymmetric synthesis of 1-aminocyclopropane-1-carboxylic acids (ACCs) such as allo-corononamic and allo-norcoronamic acids. The hydrogenation reaction of these systems at ambient pressure in the presence of formaldehyde affords saturated oxazinones and N-methylated oxazinones which have been transformed into the N-methyl-α-amino acids (N-MAAs) (S)-2-(methylamino)butanoic acid and (S)-N-methylleucine. In addition, the parent α,β-didehydroalanine derivative 11g has been prepared by a direct aminomethylation-elimination sequence from 7 and Eschenmoser's salt and has been used in Diels-Alder cycloaddition with endo selectivity for the synthesis of the enantiomerically pure bicyclic α-amino acids (-)-2-aminobicyclo[2.2.1]heptane-2-carboxylic and (-)-2-aminobicyclo[2.2.2]octane-2-carboxylic acids.

Asymmetric synthesis of bicyclic α-amino acids by a Diels-Alder reaction to a new chiral α,β-didehydroalanine derivative

A new chiral cyclic α,β-didehydroalanine derivative, (6S)-6-isopropyl- 3-methylene-5-phenyl-3,6-dihydro-2H-1,4-oxazin-2-one, has been prepared by in situ aminomethylation-elimination of a chiral glycine-derived precursor. This oxazin-2-one acts as a react

Asymmetric synthesis of substituted 1-aminocyclopropane-1-carboxylic acids from a new chiral glycine equivalent with 3,6-dihydro-2H-1,4-oxazin-2- one structure

Condensation of the new chiral glycine equivalent 10 with aldehydes at room temperature in the presence of K2CO3 under solid-liquid phase- transfer-catalysed conditions afforded stereoselectively new chiral (Z)- α,β-didehydroamino ac