94992-81-1Relevant academic research and scientific papers
The C2 selective nucleophilic substitution reactions of 2,3-epoxy alcohols mediated by trialkyl borates: The first endo-mode epoxide-opening reaction through an intramolecular metal chelate
Sasaki, Minoru,Tanino, Keiji,Hirai, Atsushi,Miyashita, Masaaki
, p. 1789 - 1791 (2007/10/03)
(Matrix presented) Highly efficient C2 selective substitution reactions of 2,3-epoxy alcohols with nucleophiles were developed by using NaN 3-(CH3O)3B, NaSPh-(CH3O) 3B, or NaCN-(C2H5/
Determination of absolute configurations of β-or γ-methyl substituted secondary alcohols by NMR spectroscopy
Takahashi, Haruko,Iwashima, Makoto,Iguchi, Kazuo
, p. 333 - 336 (2007/10/03)
A new method has been developed for determining the absolute configurations of acyclic β- or γ-methyl substituted secondary alcohols using their 2NMA esters. The 1H-NMR spectra of (R)- and (S)-2NMA esters of model compounds were measured, and Δδ values (δ(R-ester) - δ(S-ester) for the corresponding protons were compared between syn and anti compounds. Threshold values important to judging the relative stereochemistry of the two chiral centers bearing methyl and hydroxy groups were obtained. The absolute configuration of the chiral bearing a secondary hydroxy group is easily determined based on the sign of Δδ values as in the MTPA method and thus in the present study it was also possible to clearly determine the absolute configuration of the chiral center bearing a methyl group.
PHEROMONE CHIRALITY OF AFRICAN PALM WEEVIL, Rhynchophorus phoenicis (F.) AND PALMETTO WEEVIL, Rhynchophorus cruentatus (F.) (COLEOPTERA: CURCULIONIDAE)
Perez, Alice L.,Gries, Gerhard,Gries, Regine,Giblin-Davis, Robin M.,Oehlschlager, A. Cameron
, p. 2653 - 2672 (2007/10/03)
There are four stereoisomers of both 3-methyl-octan-4-ol, the aggregation pheromone of the African palm weevil, Rhynchophorus phoenicis (F.) and 5-methyl-octan-4-ol, the aggregation pheromone of the palmetto weevil, Rhynchophorus cruentatus (F.). Synthetic stereoisomers of 3-methyl-octan-3-ol and 5-methyl-octan-4-ol were baseline-separated on a Cyclodex-B fused silica column. Use of this column in gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometric (GC-MS) analyses revealed that only one stereoisomer, (3S,4S)-3-methyl-octan-4-ol and (4S,5S)-5-methyl-octan-4-ol, is produced by male R. phoenicis and male R. cruentatus, respectively, and elicits good antennal responses by conspecific male and female weevils. In field trapping experiments, with R. phoenicis in Cote d'Ivoire and R. cruentatus in Florida, (3S,4S)-3-methyl-octan-4-ol and (4S,5S)-5-methyl-octan-4-ol strongly enhanced attraction of fresh palm tissue, whereas other stereoisomers were behaviorally benign. Stereoisomeric 3-methyl-octan-4-ol and 5-methyl-octan-4-ol may be utilized to monitor and/or manage populations of these two palm weevils. - Keywords: Coleoptera, Curculionidae, Rhynchophorus phoenicis, Rhynchophorus cruentatus, aggregation pheromone, pheromone chirality, (3S,4S)-3-methyl-octan-4-ol, (3R,4R)-3-methyl-octan-4-ol, (3S,4R)-3-methyl-octan-4-ol, (3R,4S)-3-methyl-octan-4-ol, (4S,5S)-5-methyl-octan-4-ol, (4R,5R)-5-methyl-octan-4-ol, (4S,5R)-5-methyl-octan-4-ol, (4R,5S)-5-methyl-octan-4-ol
TOTAL SYNTHESIS OF THE UNUSUAL CYCLOSPORINE AMINO ACID MeBMT
Tung, Roger D.,Rich, Daniel H.
, p. 1139 - 1142 (2007/10/02)
Sharpless epoxidation of the readily available dienol 2, followed by regiospecific opening with Me2CuLi/BF3*Et2O yields, after protecting group manipulation, the mono protected diol 10c.Swern oxidation gives the cyclic carbaminol 14a which is easily manip
