On the possibility of determining stereochemistry in acyclic polyhydroxylated compounds by the combined vicinal coupling constant/molecular mechanics method. A test with alditol peracetates
✍ Scribed by Eiji Ōsawa; Keisuke Imai; Teruyo Fujiyoshi-Yoneda; Carlos Jaime; Philip Ma; Satoru Masamune
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- French
- Weight
- 655 KB
- Volume
- 47
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
Vicinsl tH-tH coupling constants on the bsckbone carbon chain of several slditol and deoxyalditol peracetates were calculated with a multipamm&ic extension of Ksrplus equation, using conformer distributions and stmctusl information obtained by energy-minimizing all of the mtmners along the backbone chsin MM2(85). The population-weighted couplii constsnts sgreed moderately well with the observed: the standard deviation of errors in reproducing 160 experimental coupling constants was 0.74 Hz. A root-mean-square test indicates that, if a gross stnrcture of an slditol or relstai compound is known, the combii NMR analysis snd MM calculations can predict relative Conflgurstions for all stereogenie centres of the molecule with a success rate of 92%.