168336-52-5

Upstream product

• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 1066-54-2 trimethylsilylacetylene 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 6207-45-0 2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran 

Downstream Products

• 1384643-86-0 C₄₄H₄₁NO₉ 
• 1384643-88-2 C₄₃H₄₁NO₈ 
• 1384643-90-6 C₄₃H₄₃NO₆ 
• 1384643-91-7 C₄₃H₄₃NO₆ 
• 1384643-96-2 C₄₅H₄₄N₂O₆ 
• 168105-48-4 C₇₂H₇₀O₁₀ 
• 141196-28-3 trimethyl(((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)ethynyl)silane 
• 168253-07-4 (2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-ethynyl-tetrahydro-pyran 

Relevant academic research and scientific papers

Total synthesis of indole-3-acetonitrile-4-methoxy-2-C-β-d- glucopyranoside. Proposal for structural revision of the natural product

Indole-3-acetonitrile-4-methoxy-2-C-β-d-glucopyranoside (1), a novel C-glycoside from Isatis indigotica with important cytotoxic activity, has been prepared in ten steps from ethynyl-β-C-glycoside 3 and 2-iodo-3-nitrophenyl acetate 6. Key steps in the synthesis include a Sonogashira coupling and a CuI-mediated indole formation. NMR spectroscopic data for synthetic 1 differs from that reported for the natural product. A revised structure for the natural product, containing an alternate carbohydrate substituent, is proposed. The Royal Society of Chemistry 2012.