Bedoukian   RussellIPM   Laser Vibrometer

Animal Taxa
Plant Taxa
Floral Compounds
Semiochemical Detail
Semiochemicals & Taxa


Invasive spp.
Email to a Friend
Kindly Donate for The Pherobase
« Previous Compound3S4R-E,Z-faranal    Next Compound »3S4Sme-hexan-3-ol
Compound - 3S4Sme-heptan-3-ol


Discuss this Compound    Help


Formula: C8H18O 
MW: 130.23 

[MS]  [ NMR ]  [Behavioural function]  [Chemdraw

Dots surface:

Reference(s) for synthesis of (3S,4S)-4-Methylheptan-3-ol

Einterz, R.M., Ponder, J.W., and Lenox, R.S. 1977. The synthesis of 4-methyl-3-heptanol and 4-methyl-3-heptanone. J. Chem. Educ. 54:382.
Frater, G. 1979. Stereospezifische synthese von (9+)-(3R,4R)-4-methyl-3-heptanol, das enantiomere eines pheromons des kleinen Ulmensplintkaefers (Scolytus multistriatus). Helv. Chim. Acta. 62:2829.
Fuganti, C., Grasselli, P., Servi, S., and Zirotti, C. 1982. Synthesis of the enantiomeric forms of cis and trans 1-benzyloxy-2,3-epoxy butane and of (3S,4S)-4-methyl-3-heptanol. Tetrahedron Lett. 23:4269-4272.
Fujisawa, T., Tajima, K., and Sato, T. 1984. Chirality transfer in the ester enolate Claisen rearrangement of (R)-1-methyl-(E)-2-butenyl hydroxyacetate and its application to the stereocontrolled pheromone synthesis. Chem. Lett. 1669.
Hoffmann, R.W., Ladner, W., and Helbig, W. 1984. Stereoselektive Synthese von alkoholen. XVIII. Synthese von (3S,4S)-4-methyl-3-heptanol und von (5S,6S)-anhydro-serricornin. Liebigs Ann. Chem. 1170.
Koreeda, M., and Tanaka, Y. 1982. Stereoselective acyclic synthesis via allylmetals: an efficient synthesis of ()-4methylheptan-3-ol, an aggregation pheromone of the smaller European elm bark beetle. Chem. Lett. 1297-1298.
Matteson, D.S., and Sadhu, K.M. 1983. Boronic ester homologation with 99% chiral selectivity and its use in syntheses of the insect pheromones (3S,4S)-4-methyl-3-heptanol and exo-brevicomin. J. Am. Chem. Soc. 105:2077-2078.
Matteson, D.S., Sadhu, K.M., and Peterson, M.L. 1986. 99% Chirally selective syntheses via pinanediol boronic esters: insect pheromones, diols, and an amino alcohol. J. Am. Chem. Soc. 108:810-819.
Mori, K. 1977. Absolute configuration of (-)-4-methylheptan-3-ol, a pheromone of the smaller European elm bark beetle, as determined by the synthesis of its (3R,4R)-(+)- and (3S,4R)-(+)- isomers. Tetrahedron. 33:289-294.
Mori, K., and Iwasawa, H. 1980. Preparation of the both enantiomers of threo-2-amino-3-methylhexanoic acid by enzymatic resolution and their conversion to optically active forms of threo-4-methylheptan-3-ol, a pheromone component of the smaller European elm bark beetle. Tetrahedron. 36:2209-2213.
Nakagawa, N., and Mori, K. 1984. Synthesis of (3S,4S)-4-methyl-3-heptanol and its (3S,4R)-isomer employing asymmetric epoxidation coupled with regioselective cleavage of epoxides with trimethylaluminum. Agric. Biol. Chem. 48:2505.
Narasaka, K., and Miwa, T. 1985. Highly enantioselective synthesis of anti (threo)-aldols by the asymmetric aldol reaction utilizing a chiral azaenolate. Chem. Lett. 1217.
Pearce, G.T., Gore, W.E., Silverstein, R.M., Peacock, J.W., Cuthbert, R.A., Lanier, G.N., and Simeone, J.B. 1975. Chemical attractants for the smaller European elm bark beetle Scolytus multistriatus (Coleoptera: Scolytidae). J. Chem. Ecol. 1:115-124.
Plummer, E.L., Stewart, T.E., Byrne, K., Pearce, G.T., and Silverstein, R.M. 1976. Determination of the enantiomeric composition of several insect pheromone alcohols. J. Chem. Ecol. 2:307.
Pougny, J.-R., and Sinay, P. 1982. (3S,4S)-4-Methylheptan-3-ol, a pheromone component of the smaller European elm bark beetle: synthesis from D-glucose. J. Chem. Res. 1:186-196.
Rossi, R., and Marasco, M. 1980. Insect pheromones by asymmetric synthesis. Asymmetric synthesis of (S)-4-methyl-3-heptanone, the alarm pheromone of Atta texana, of (4S)-4-methyl-3-heptanol, the major aggregation pheromone component of Scolytus scolytus, and of (S)-3-methyl-2-heneicosanone, a structural analogue of a sex pheromone component of Blattella germanica. Chim. Ind. (Milano). 62:314.
Sayo, N., Azuma, K.-I., Mikami, K., and Nakai, T. 1984. Acyclic stereocontrol via asymmetric [2,3]-Wittig rearrangement with high enantio- and erythro-selectivity and its use in the chiral synthesis of insect pheromones. Tetrahedron Lett. 25:565-568.
Schlosser, M., and Fujita, K. 1982. A stereocontrolled synthesis of the pheromone 4-methyl-3-heptanol: novel and selective cc-linking reactions. Angew. Chem. Int. Ed. Engl. 21:309-310.
Steiger, B., Wadder, L., and Scheffold, R. 1986. Sonnenenergie in der organischen chemie: photokatalytische elektrosynthese eines pheromone. Chimia. 40:93.

Citation: El-Sayed AM 2018. The Pherobase: Database of Pheromones and Semiochemicals. <>.
2003-2018 The Pherobase - Extensive Database of Pheromones and Semiochemicals. Ashraf M. El-Sayed.
Page created on 5-January-2018