Synthesis of orthogonally protected (2R,3R,4S)-4-amino-2,3-dihydroheptan-1,7-dioic acid.
Synthesis of orthogonally protected (2R,3R,4S)-4-amino-2,3-dihydroheptan-1,7-dioic acid.
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正交保护的(2R,3R,4S)-4-氨基-2,3-二氢庚-1,7-二酸的合成。
DOI：
10.1055/s-0034-1378902
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发表时间：
2015
期刊：
影响因子：
--
通讯作者：
H.
中科院分区：
文献类型：
--
作者：
Tokairin;Y.; Maita;K.; Takeda;S.; Konno;H.
(2R以Fmoc-Glu（t-Bu）-OH为起始原料，经6步反应合成了具有抗HIV活性的环缩肽类高卟啉化合物中的一个重要组成部分--（3R，4S）-4-氨基-2，3-二羟基庚烷-1，7-二酸。锇催化γ-氨基-Z-α，β-不饱和酯的双羟基化反应，以中等的非对映选择性得到了二羟基酯。通过比较1HNMR谱确定了氨基酸的立体化学。
(2R,3R,4S)-4-Amino-2,3-dihydroxyheptane-1,7-dioic acid, a common component of cyclic depsipeptide homophymines with anti-HIV activity, was synthesized as its orthogonally protected derivative from Fmoc-Glu(t-Bu)-OH in 6 steps. Osmium-catalyzed dihydroxylation of γ-amino-Z-α,β-unsaturated esters gave the dihydroxy esters with moderate diastereoselectivity. The stereochemistries of the amino acids were determined by comparison of1H NMR spectra.