77564-41-1Relevant academic research and scientific papers
Pheromone synthesis. Part 256: Synthesis of the four stereoisomers of 5,11-dimethylpentacosane, a new sex pheromone component of the male Galleria mellonella (L.), with high stereochemical purities as determined by the derivatization-HPLC analysis of the eight stereoisomers of 5,11-dimethyl-8-pentacosanol
Mori, Kenji,Akasaka, Kazuaki
, p. 4102 - 4115 (2015/06/02)
Abstract All the four stereoisomers of 5,11-dimethylpentacosane (>96.8% purity) were synthesized via the stereoisomers of 5,11-dimethyl-8-pentacosanol, whose stereoisomeric compositions could be determined precisely by their low temperature HPLC analysis after derivatization. 5,11-Dimethyl-8-pentacosanol was prepared by a Grignard reaction between 3-methylheptylmagnesium bromide and 4-methyloctadecanal, both of which were prepared from the commercially available enantiomers of citronellal (97-98% ee). Alternatively, (R)-3-methyl-1-heptanol could be prepared from methyl (R)-3-hydroxybutanoate (100% ee). Pd/C-catalyzed hydrogenation of a 5-methyl-1-alkene caused partial racemaization at C-5.
STEREOCONTROL BY INTRODUCTION OF A SULFUR FUNCTIONAL GROUP IN THE ASYMMETRIC REDUCTION OF β-KETOESTERS WITH BAKER'S YEAST: PREPARATION OF OPTICALLY PURE 3S-HYDROXYDITHIOESTERS AS A NEW CHIRAL SYNTHON OF NATURAL PRODUCT SYNTHESIS
Itoh, Toshiyuki,Yonekawa, Yoshihiro,Sato, Toshio,Fujisawa, Tamotsu
, p. 5405 - 5408 (2007/10/02)
Asymmetric reduction of β-ketothioester derivatives with baker's yeast produced the corresponding optically pure 3S-hydroxythioesters, which are useful chiral building blocks in organic synthesis.The utility of the present method was demonstrated in the stereoselective synthesis of sex attractant of pine saw-fly, (2S,3S,7S)-3,7-dimethylpentadec-2-yl acetate from the 3S-hydroxy esters.
SYNTHESIS OF TREE STEREOISOMERIC FORMS OF 2,8- DIMETHYL-1,7-DIOXASPIROUNDECANE, THE MAIN COMPONENT OF THE CEPHALIC SECRETION OF ANDRENA WILKELLA
Mori, Kenji,Tanida, Kaichi
, p. 3221 - 3225 (2007/10/02)
Three stereoisomers of 2,8-dimethyl-1,7-dioxaspiroundecane were synthesized from acetoacetic ester by utilizing its yeast reduction and dianion alkylation.
SYNTHESIS OF THREE STEREOISOMERIC FORMS OF 2,8-DIMETHYL-1,7-DIOXASPIROUNDECANE, THE MAIN COMPONENT OF THE CEPHALIC SECRETION OF ANDRENA WILKELLA
Mori, Kenji,Tanida, Kaichi
, p. 1171 - 1174 (2007/10/02)
Three stereoisomers of 2,8-dimethyl-1,7-dioxaspiroundecane with defined stereochemistry at C-2 and C-8 were synthesized utilizing yeast reduction and dianion alkylation of ethyl acetoacetate.
