791765-20-3

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 202577-85-3 3-(4-Benzyloxy-3-chloro-phenyl)-3-hydroxy-propionic acid ethyl ester 
• 202577-82-0 3-(4-Benzyloxy-3-chloro-phenyl)-3-oxo-propionic acid ethyl ester 
• 2420-16-8 4-hydroxy-3-chlorobenzaldehyde 
• 159526-70-2 (2R,3R)-2-Azido-3-(4-benzyloxy-3-chloro-phenyl)-3-hydroxy-propionic acid ethyl ester 
• 66422-84-2 4-benzyloxy-3-chlorobenzaldehyde 

Relevant academic research and scientific papers

Solid-phase synthesis using (Allyloxy)carbonyl(Alloc) chemistry of a putative heptapeptide intermediate in vancomycin biosynthesis containing m-chloro-3-hydroxytyrosine

A convenient method for the solid-phase synthesis of putative linear heptapeptide intermediates in vancomycin biosynthesis is described, in particular, the heptapeptide D-Leu-Cyt-L-Asn-Hpg-Hpg-Cyt'-Dhpg (Cyt = (2R,3R)-m-chloro-3-hydroxytyrosine, Hpg = (R)-2-(p-hydroxyphenyl)glycine, Cyt' = (2S,3R)-m-chloro-3-hydroxytyrosine and Dhpg = (S)-2-(3,5-dihydroxyphenyl)glycine). The synthesis was performed on chlorotrityl resin and employed the (allyloxy)carbonyl protecting group for temporary N(α) protection during peptide-chain assembly.

Baker's yeast mediated enantiospecific synthesis of anti-(2R,3R)-p-chloro-3-hydroxytyrosine: An α-amino-β-hydroxy acid of vancomycin

Baker's yeast mediated reduction of α-azido-β-keto ester lead to reduction of the carbonyl group with high enantiospecificity and diastereoselectivity at low pH (4.0, e.e. >99%, d.e. 79%). At pH ~7, although the enantioselectivity is maintained, the diastereoselectivity is lost.