Guaragna Annalisa, Napolitano Carmela, D'Alonzo Daniele, Pedatella Silvana, Palumbo Giovanni
Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, via Cynthia, 4 I-80126 Napoli, Italy.
Org Lett. 2006 Oct 12;8(21):4863-6. doi: 10.1021/ol061916z.
[reaction: see text] An efficient route for the synthesis of orthogonally protected l-sugars has been opened up, starting from the heterocyclic homologating agent 1 and 2,3-O-isopropylidene-l-glyceraldehyde (2). Our synthetic path enables the synthesis of a 2,3-unsaturated-l-pyranoside, which can be suitably functionalized to afford the desired l-hexoses. In this paper, we report the synthesis of l-manno- and l-altro-pyranosides. Moreover, this strategy may be used to prepare all eight sugars and their derivatives in either enantiomeric form.
[反应：见正文] 从杂环同系化试剂1和2,3-O-异亚丙基-l-甘油醛（2）出发，开辟了一条合成正交保护的l-糖的有效路线。我们的合成路径能够合成2,3-不饱和-l-吡喃糖苷，其可进行适当的官能化以得到所需的l-己糖。在本文中，我们报道了l-甘露糖基和l-阿卓糖基吡喃糖苷的合成。此外，该策略可用于制备所有八种糖及其对映体形式的衍生物。
