58108-99-9

Upstream product

• 58109-01-6 5-hydroxy-7-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2-methylchromone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 144152-27-2 1-[2,4,6-tris(acetyloxy)phenyl]ethanone 
• 1013-69-0 eugenin 

Downstream Products

• 294856-66-9 cypellocarpin C 
• 1274775-58-4 7-O-(2,3,4-tri-O-acetyl-6-trityl-β-D-glucopyranosyl)-5-hydroxy-2-methylchromone 

Relevant academic research and scientific papers

Concise synthesis of 5-methoxy-6-hydroxy-2-methylchromone-7-O- and 5-hydroxy-2-methylchromone-7-O-rutinosides. Investigation of their cytotoxic activities against several human tumor cell lines

The synthesis of two novel 2-methylchromone-7-O-rutinosides is reported, and the in vitro biological activities of these compounds and their synthetic precursors have been investigated on the basis of their cytotoxicity against several human tumor cell lines. The synthesis features early stage assembly of the acidic labile glycosidic bond between sugar and 2-methylchromone aglycon under phase transfer catalyzed glycosidation conditions, whereas all the other standard glycosylation conditions specific to a wide array of rutinosyl donors bearing different anomeric leaving groups (e.g., SPh, OC(NH)CCl3, Br, OH groups) failed to furnish any detectable products.

Synthesis of the monoterpenoid esters cypellocarpin C and cuniloside B and evidence for their widespread occurrence in Eucalyptus

Short syntheses of cuniloside B and cypellocarpin C, (+)-(R)-oleuropeic acid-containing carbohydrates, are reported. Also disclosed are syntheses of the noreugenin glycosides, undulatoside A and corymbosins K1 and K 2. Leaf extracts of 28 diverse eucalypts revealed cuniloside B to be present in all, and cypellocarpin C to be present in most, of the species examined. The widespread occurrence of these carbohydrate monoterpenoid esters supports their roles in essential oil biosynthesis or mobilization from sites of synthesis to secretory cavity lumena.