4-取代-1,2-二氧六环的二羟基化反应：一种合成支链赤藓糖的简洁方法。
Dihydroxylation of 4-substituted 1,2-dioxines: a concise route to branched erythro sugars.
作者信息
Robinson Tony V, Pedersen Daniel Sejer, Taylor Dennis K, Tiekink Edward R T
机构信息
Department of Chemistry, The University of Adelaide, South Australia 5005, Australia.
出版信息
J Org Chem. 2009 Jul 17;74(14):5093-6. doi: 10.1021/jo900669u.
The synthesis of 2-C-branched erythritol derivatives, including the plant sugar (+/-)-2-C-methylerythritol 2, was achieved through a dihydroxylation/reduction sequence on a series of 4-substituted 1,2-dioxines 3. The asymmetric dihydroxylation of 1,2-dioxines was examined, providing access to optically enriched dihydroxy 1,2-dioxanes 4. The synthesized 1,2-dioxanes were converted to other erythro sugar analogues and tetrahydrofurans through controlled cleavage of the endoperoxide linkage.
通过对一系列4-取代的1,2-二氧六环3进行双羟基化/还原序列反应，实现了2-C-支链赤藓糖醇衍生物的合成，其中包括植物糖(±)-2-C-甲基赤藓糖醇2。对1,2-二氧六环的不对称双羟基化反应进行了研究，从而得到了光学富集的二羟基1,2-二氧杂环己烷4。通过对过氧化环醚键的可控裂解，将合成得到的1,2-二氧杂环己烷转化为其他赤藓糖类似物和四氢呋喃。
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