187746-38-9

Upstream product

• 187746-36-7 C₃₀H₃₉NO₉ 
• 319493-93-1 (3S,3aR,6aS)-3-(4-Methoxy-phenyl)-1-((R)-1-phenyl-ethyl)-tetrahydro-furo[3,4-c]isoxazol-6-one 
• 53484-50-7 (E)-p-methoxy-cinnamyl alcohol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 187746-37-8 (3S,4R,5S)-3-Amino-4-hydroxymethyl-5-(4-methoxy-phenyl)-dihydro-furan-2-one 

Downstream Products

• 319493-96-4 (2S,3R)-4-Acetoxy-2-tert-butoxycarbonylamino-3-(4-methoxy-benzyl)-butyric acid methyl ester 
• 319493-95-3 (2S,3R)-4-Acetoxy-2-tert-butoxycarbonylamino-3-(4-methoxy-benzyl)-butyric acid 

Relevant academic research and scientific papers

Stereocontrolled synthesis of multi-functionalized β-substituted α-amino acids: Nitrone cycloaddition approach

Syn- and anti-β-substituted α-amino acids 1 and 2 were synthesized by employing nitrone-cycloaddition. The stereochemistries required were controlled via a (Z)-nitrone-exo transition state for syn-amino acid 1 and via an (E)-nitrone-exo transition state for anti-amino acid 2, respectively.

Intramolecular cycloaddition of α-allyloxycarbonylnitrone bearing a chiral sugar auxiliary: A short-step synthesis of the N-terminal amino acid component of nikkomycin Bz

Heating 2,3:5,6-O-dicyclohexylidene-L-gulose oxime with methyl glyoxylate hemiacetal followed by treatment of the resulting mixture with allyl alcohols in the presence of catalytic amounts of titanium tetrachloride and molecular sieves 4A caused tandem nitrone formation, transesterification, E,Z-isomerization and diastereofacial selective intramolecular cycloadditian to provide stereocontrolled polycyclic compounds in one step. This method could be applied efficiently to synthesis of the N-terminal amino acid component of nikkomycin Bz.