59679-95-7Relevant academic research and scientific papers
Asymmetric synthesis of (2R)- and (2S)-2-iodohexadecanal, natural inhibitors of the thyroid gland metabolism
Jacoby, Claude,Braekman, Jean-Claude,Daloze, Desire
, p. 10473 - 10484 (2007/10/03)
(2R)-(+)- and (2S)-(-)-2-iodohexadecanal 1 with ee's≤89% were synthesized in five steps and 62% overall yield from chiral enol ethers Z- and/or E-7, via the iodocyclization with ICl and chromatographic separation of the resulting diastereomeric 1'-iododioxanes 8. The ee's of (2S)- and (2R)-1 have been determined after their transformation to the (R)-O-methylmandelate esters 11 and 12 or to the epoxides (2R)- and (2S)-13, respectively. Their absolute configuration has been assigned through chemical correlation with 13 and by application of Mosher's method to the esters 15 and 16 obtained by methanolysis of (2R)- and (2S)-13, respectively, followed by derivatization. Moreover, the biosynthesis and the inhibitory activity of 1 have been shown to be unstereoselective.
Reaction of Hydrogen Halides with 1,2-Hexadecanediol
Ahmad, M. S.,Khan, Mushfiquddin,Osman, S. M.
, p. 1001 - 1002 (2007/10/02)
Reaction of 1,2-hexadecanediol (I) with hydrochloric acid in the presence of acetic anhydride gives a mixture of 2-acetoxy-1-hydroxyhexadecane (III) and 1,3-hexadecanediol (V).However, a similar treatment of I with hydroiodic acid in the presence of acetic anhydride furnishes 1-iodo-2-acetoxyhexadecane (VII), 1,2-diacetoxyhexadecane (VI) and 1-acetoxy-2-hydroxyhexadecane (IV).Structures of the products III, IV, V, VI and VII have been established on the basis of elemental analyses, spectral data and chemical evidence.
