413598-71-7

Upstream product

• 413598-70-6 (R)-4-Benzyl-3-((E)-(2S,3S)-3-methoxymethoxy-2-methyl-hex-4-enoyl)-oxazolidin-2-one 
• 413598-51-3 (4R)-3-[(2S,3S,4E)-2-methyl-1-oxo-3-hydroxy-4-hexenyl]-4-phenylmethyl-2-oxazolidinone 
• 98-59-9 p-toluenesulfonyl chloride 
• 413598-52-4 (E)-(2R,3S)-3-Methoxymethoxy-2-methyl-hex-4-en-1-ol 

Downstream Products

• 413598-68-2 (2S,3R,5S)-5-[(1R,2R,3R)-2,5-Bis-methoxymethoxy-3-methyl-1-(2-trimethylsilanyl-ethoxymethoxy)-pentyl]-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carbaldehyde 
• 413598-69-3 (E)-4-[(2R,3R,5S)-5-[(1R,2R,3R)-2,5-Bis-methoxymethoxy-3-methyl-1-(2-trimethylsilanyl-ethoxymethoxy)-pentyl]-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-but-3-en-2-one 
• 794515-82-5 (S)-1-[(2R,3R,5S)-5-[(1R,2R,3R)-2,5-Bis-methoxymethoxy-3-methyl-1-(2-trimethylsilanyl-ethoxymethoxy)-pentyl]-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-ethane-1,2-diol 
• 413598-67-1 (2-{(1R,2R,3R)-1-[(2S,4R,5S)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,5-bis-methoxymethoxy-3-methyl-pentyloxymethoxy}-ethyl)-trimethyl-silane 

Relevant academic research and scientific papers

Alkoxide precoordination to rhodium enables stereodirected catalytic hydrogenation of a dihydrofuranol precursor of the C29-40 F/G sector of pectenotoxin-2

An enantioselective synthesis of the stereochemically fully endowed C(29-40) fragment of pectenotoxin-2 is detailed. The highlight of the synthesis is an alkoxide-directed hydrogenation in which ionic complexation of the deprotonated substrate to [Rh(NBD)(DIPHOS-4)]BF4, accomplished by the co-addition of an equivalent of sodium hydride in THF, completely deters a kinetic tendency for dehydration and properly sets the critical stereochemistry at C-35. The dual objectives made possible by this catalytic technology are expected to have far-ranging applications. Graphical Abstract.

Pectenotoxin-2 synthetic studies. 1. Alkoxide precoordination to [Rh(NBD)(DIPHOS-4)]BF4 allows directed hydrogenation of a 2,3-dihydrofuran-3-ol without competing furan production

(equation presented) The alkoxide-directed hydrogenation shown is reported as a key step in a concise synthesis of a fully functionalized precursor to the C29-C40 F/G sector of pectenotoxin-2.