Unknown

Dataset Information

0

Synthesis and analysis of the all-(S) side chain of phosphomycoketides: a test of NMR predictions for saturated oligoisoprenoid stereoisomers.


ABSTRACT: (4S,8S,12S,16S,20S)-Pentamethylheptacosan-1-ol has been synthesized and analyzed by resolution-enhanced NMR spectroscopy with the aid of a recent set predicted spectra of all its stereoisomers. The configuration was confirmed, but isomer purity of the sample (~70%) was lower than expected. A truncated analogue, (2S,6S,10S,14S)-2,6,10,14-tetramethylhenicosan-1-ol TBDPS ether, was prepared from a late stage synthetic intermediate. Analysis of its spectra confirmed the configuration and showed that the sample was isomerically pure. The results suggest that a late-stage epimerization, not a failure of an asymmetric synthesis step, caused the formation of minor stereoisomers in the sample of pentamethylheptacosan-1-ol. The study shows the value of the predicted set of oligoisoprenoid spectra and further extends the predictive model to a new subclass of compounds.

SUBMITTER: Buter J 

PROVIDER: S-EPMC3714862 | biostudies-literature | 2013 May

REPOSITORIES: biostudies-literature

altmetric image

Publications

Synthesis and analysis of the all-(S) side chain of phosphomycoketides: a test of NMR predictions for saturated oligoisoprenoid stereoisomers.

Buter Jeffrey J   Yeh Edmund A-H EA   Budavich Owen W OW   Damodaran Krishnan K   Minnaard Adriaan J AJ   Curran Dennis P DP  

The Journal of organic chemistry 20130425 10


(4S,8S,12S,16S,20S)-Pentamethylheptacosan-1-ol has been synthesized and analyzed by resolution-enhanced NMR spectroscopy with the aid of a recent set predicted spectra of all its stereoisomers. The configuration was confirmed, but isomer purity of the sample (~70%) was lower than expected. A truncated analogue, (2S,6S,10S,14S)-2,6,10,14-tetramethylhenicosan-1-ol TBDPS ether, was prepared from a late stage synthetic intermediate. Analysis of its spectra confirmed the configuration and showed that  ...[more]

Similar Datasets

| S-EPMC3560418 | biostudies-literature
| S-EPMC2143120 | biostudies-other
| S-EPMC2684938 | biostudies-literature
| S-EPMC4654418 | biostudies-literature
| S-EPMC8715507 | biostudies-literature
| S-EPMC8571068 | biostudies-literature
| S-EPMC7734624 | biostudies-literature
| S-EPMC5441803 | biostudies-literature
| S-EPMC8480538 | biostudies-literature
| S-EPMC4470380 | biostudies-literature