Analysis of two carbon-13 NMR correlations for determining the stereochemistry of 1,3-diol acetonides

Analysis of two carbon-13 NMR correlations for determining the stereochemistry of 1,3-diol acetonides
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分析两个碳 13 NMR 相关性以确定 1,3-二醇丙酮化合物的立体化学

DOI:
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发表时间:
1993
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影响因子:
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通讯作者:
Guang Yang
Guang Yang
中科院分区:
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文献类型:
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作者:
S. Rychnovsky;Bruce N. Rogers;Guang Yang

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顺式和反式1,3-二醇丙酮化物的立体化学可以根据缩醛甲基的 13 C 化学位移和缩醛碳的 13 C 化学位移来确定。一般来说,顺式1,3-二醇丙酮化物的缩醛甲基位移为19和30 ppm,缩醛碳位移为98.5 ppm,而反丙酮化物的甲基位移为25 ppm,缩醛位移为100.5 ppm。我们通过对 1,3-二醇丙酮化合物进行完整的文献检索并识别具有可分配 13 C 光谱的文献,测试了这两种相关性的普遍性和可靠性
The stereochemistry of syn- and anti-1,3-diol acetonides can be assigned from the 13 C chemical shifts of the acetal methyl groups and from the 13 C chemical shifts of the acetal carbon. In general, the syn-1,3-diol acetonides have acetal methyl shifts at 19 and 30 ppm and acetal carbon shifts at 98.5 ppm, while the anti-acetonides have methyl shifts at 25 ppm and acetal shifts at 100.5 ppm. We have tested the generality and reliability of these two correlations by carrying out a complete literature search for 1,3-diol acetonides and identifying those with assignable 13 C spectra