Recommanded Product: Octadecan-9-olOn November 30, 2014 ,《A general method for the synthesis of enantiopure aliphatic chain alcohols with established absolute configurations. Part 2, via catalytic reduction of acetylene alcohol MαNP esters》 appeared in Tetrahedron: Asymmetry. The author of the article were Akagi, Megumi; Sekiguchi, Satoshi; Taji, Hiromi; Kasai, Yusuke; Kuwahara, Shunsuke; Watanabe, Masataka; Harada, Nobuyuki. The article conveys some information:
A general method for synthesizing enantiopure (100% ee) aliphatic alcs. with established absolute configurations has been developed and applied to alcs. CH3(CH2)n-CH(OH)-(CH2)mCH3, the enantiomeric discrimination of which is the most difficult, if m = n + 1 and n is large. Racemic saturated alcs. with short chains could be directly enantioresolved as (S)-(+)-2-methoxy-2-(1-naphthyl)propionic acid [MαNP acid (I)] esters by HPLC on silica gel, and their absolute configurations were simultaneously determined by 1H NMR diamagnetic anisotropy. However, the application of this powerful MαNP ester method to alcs. with long chains was difficult, because of smaller values of the separation factor α. In such cases, the use of the corresponding acetylene alc. MαNP esters was crucial. Acetylene alc. MαNP esters were largely separated by HPLC on silica gel, and their absolute configurations were unambiguously determined by 1H NMR as reported in the Part 1 paper. The MαNP esters obtained with established absolute configurations were catalytically hydrogenated to yield saturated alc. MαNP esters. It was evidenced that no racemization occurred at the stereogenic center of the alc. moiety during catalytic hydrogenation, by the co-injection of MαNP esters in HPLC. From the MαNP esters obtained, enantiopure (100% ee) aliphatic chain alcs. with established absolute configurations were recovered. Although the [α]D values of these alcs. were too small for the identification of the enantiomers, it was clarified that the anal. HPLC of MαNP esters is useful for identification in most cases. In the experimental materials used by the author, we found Octadecan-9-ol(cas: 591-70-8Recommanded Product: Octadecan-9-ol)
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Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts