150620-86-3

Upstream product

• 3761-92-0 n-hexylmagnesium bromide 
• 14618-80-5 (R)-benzyl glycidol 
• 111-25-1 1-bromo-hexane 

Downstream Products

• 150620-87-4 (R)-1-O-Benzyl-2-O-(tert-butyldimethylsilyl)nonane-1,2-diol 
• 208589-17-7 (2R)-toluene-4-sulfonic acid 2-hydroxynonyl ester 
• 118969-84-9 (R)-Nonane-1,2-diol 
• 28114-20-7 R-(+)-1,2-epoxynonane 

Relevant academic research and scientific papers

Synthesis and Absolute Configuration of Two Natural Phenolic Homobenzyl Esters

Two recently identified natural phenolic homobenzyl esters, isolated from Phragmipedium calurum (an orchid) and Eupatorium fortunei TURCZ (a perennial herb in the Asteraceae family), respectively, were synthesized in enantiopure forms. By comparison of the optical rotations for the synthetic and the natural samples, the absolute configurations for the natural products were reliably assigned. The synthesis also enables establishment of the absolute configuration of a closely related natural homobenzyl alcohol and provided for the first time complete physical and spectroscopic data for two other natural homobenzyl esters. Two recently isolated natural phenolic homobenzyl esters were synthesized in enantiopure forms. The absolute configurations for these natural products were thus reliably assigned. En route to the total synthesis of the first target, complete physical and spectroscopic data for two other related natural products were made available for the first time. Configuration assignment of a third natural product was also achieved.

Structure and Synthesis of Petrosynes, New Acetylenic Enol Ether Glycerides from the Okinawan Marine Sponge of the Genus Petrosia

Acetylenic enol ether glycerides, 1 and 3, were found in the Okinawan marine sponge of the genus Petrosia.The plane structures of these glycerides were deduced from spectroscopic analysis.Their complete structures were established by enantioselective total synthesis of all possible stereoisomers using (R)-1-O-benzylglycerol and its (S)-enantiomer, prepared from D-mannitol and L-ascorbic acid, respectively, as chiral building blocks.The synthesis involves the palladium(0)-catalyzed coupling reaction of bromo enol ether 9 with enediyne 21 as a key step.It became evident from the synthesis that the natural product 1 consisted of a mixture of (7R,2'S)-24 (petrosyne Ia) and (7S,2'S)-24 (petrosyne Ib), and the natural product 3 consisted of a mixture of (7R,2'S)-28 (petrosyne IIa) and (7S,2'S)-28 (petrosyne IIb).