1227307-30-3

Upstream product

• 1227307-08-5 (2E,4Z)-7-((tert-butyldimethylsilyl)oxy)-8-(diethoxyphosphoryl)-5-methylocta-2,4-dienoic acid 
• 1227307-18-7 (S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy-)ethyl-)tetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-ol 
• 824-94-2 p-methoxybenzyl chloride 
• 80910-01-6 (S)-2-[(4-methoxybenzyloxy)methyl]oxirane 
• 1227307-12-1 tert-butyl-(2-((2S,4S,6S)-4-iodo-6-(prop-1-ynyl)tetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane 
• 1227307-25-6 (2E,4Z)-ethyl 7-(tert-butyldimethylsilyloxy)-8-(diethoxy phosphoryl)-5-methylocta-2,4-dienoate 
• 1227307-16-5 (Z)-diethyl 2-(tert-butyldimethyl silyloxy)-4-methyl-6-oxohex-4-enyl phosphonate 
• 1227307-24-5 (Z)-diethyl 2-(tert-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)-4-methylhex-4-enylphosphonate 
• 1227307-15-4 (Z)-diethyl 2-hydroxy-6-(4-methoxy benzyloxy)-4-methyl hex-4-enyl phosphonate 
• 1227307-35-8 C₃₈H₆₂O₂SiSn 
• 1227307-29-0 tert-butyl-(2-((2R,6S)-6-((E)-2-iodoprop-1-enyl)tetrahydro-2H-pyran-2-yl)ethoxy-)diphenylsilane 
• 1227307-28-9 tert-butyldiphenyl(2-((2R,6S)-6-(prop-1-ynyl)tetrahydro-2H-pyran-2-yl)ethoxy-)silane 
• 1227307-23-4 (Z)-2-(4-(4-methoxybenzyloxy)-2-methylbut-2-enyl)oxirane 
• 1227307-14-3 (Z)-1-chloro-6-(4-methoxybenzyloxy)-4-methylhex-4-en-2-ol 

Downstream Products

• 1227307-31-4 (2E,4Z)-((2S,E)-5-((2S,6R)-6-(2-hydroxyethyl)tetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-yl) 8-(diethoxyphosphoryl)-7-hydroxy-5-methylocta-2,4-dienoate 
• 1227307-32-5 (2E,4Z)-((S,E)-1-(4-methoxybenzyloxy)-4-methyl-5-((2S,6R)-6-(2-oxoethyl)-tetrahydro-2H-pyran-2-yl)pent-4-en-2-yl)-8-(diethoxyphosphoryl)-5-methyl-7-oxo octa-2,4-dienoate 
• 1227307-19-8 (1S,2E,5S,8E,10Z,14E,17R)-5-((4-methoxybenzyloxy)methyl)-3,11-dimethyl-6,21-dioxabicyclo [15.3.1]henicosa-2,8,10,14-tetraene-7,13-dione 

Relevant academic research and scientific papers

Total synthesis of (-)-zampanolide and structure-activity relationship studies on (-)-dactylolide derivatives

A new total synthesis of the marine macrolide (-)-zampanolide (1) and the structurally and stereochemically related non-natural levorotatory enantiomer of (+)-dactylolide (2), that is, ent-2, has been developed. The synthesis features a high-yielding, selective intramolecular Horner-Wadsworth-Emmons (HWE) reaction to close the 20-membered macrolactone ring of 1 and ent-2. The β-keto phosphonate/aldehyde precursor for the ring-closure reaction was obtained by esterification of a ω-diethylphosphono carboxylic acid fragment and a secondary alcohol fragment incorporating the THP ring that is embedded in the macrocyclic core structure of 1 and ent-2. THP ring formation was accomplished through a segment coupling Prins-type cyclization. Employing the same overall strategy, 13-desmethylene-ent-2 as well as the monocyclic desTHP derivatives of 1 and ent-2 were prepared. Synthetic 1 inhibited human cancer cell growth in vitro with nM IC50 values, while ent-2, which lacks the diene-containing hemiaminal-linked side chain of 1, is 25- to 260-fold less active. 13-Desmethylene-ent-2 as well as the reduced versions of ent-2 and 13-desmethylene-ent-2 all showed similar cellular activity as ent-2 itself. The same activity level was attained by the monocyclic desTHP derivative of 1. Oxidation of the aldehyde functionality of ent-2 gave a carboxylic acid that was converted into the corresponding N-hexyl amide. The latter showed only μM antiproliferative activity, thus being several hundred-fold less potent than 1. It's the side chain that matters: The marine macrolide (-)-zampanolide (1) has been synthesized via (-)-dactylolide (ent-2), the non-natural enantiomer of the marine natural product (+)-dactylolide (2), employing a high-yielding intramolecular Horner-Wadsworth-Emmons reaction to close the macrolactone ring. While the hemiaminal-linked side chain in 1 is crucial for nanomolar antiproliferative activity, the methylene group and the aldehyde functionality in ent-2 are dispensable. A monocyclic destetrahydropyran derivative of 1 shows equal activity as ent-2. Copyright

Synthesis of (-)-dactylolide and 13-desmethylene-(-)-dactylolide and their effects on tubulin

An efficient new synthesis has been elaborated for non-natural (-)-dactylolide ((-)-2) and its 13-desmethylene analogue 4, employing a HWE-based macrocyclization approach with β-keto-phosphonate/aldehyde 19 and the respective 13-desmethylene derivative as the key intermediates. Both (-)-2 and 4 as well as the corresponding C20 alcohols inhibit human cancer cell proliferation with IC50 values in the sub-micromolar range and induce the polymerization of tubulin in vitro.