Aza-sugars之合成：β-enaminals不預期之脫胺反應

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题名:	Aza-sugars之合成：β-enaminals不預期之脫胺反應 Synthesis of aza-sugars: Unexpected deamination of β-enaminals
作者:	周尹萱;Yin-Hsuan Chou
贡献者:	藥物化學研究所碩士班
关键词:	氮醣;乙型烯胺醛;脫胺反應;aza-sugar;β-enaminal;deamination
日期:	2013-07-31
上传时间:	2013-10-02 11:30:07 (UTC+8)
出版者:	中國醫藥大學
摘要:	3-Deoxy-C-2-formylglycals 80-81與1.1當量的一級胺（包括benzylamine, n-butylamine及n-octylamine）在甲醇的條件下反應十分鐘，可經由Michael加成反應得到3-deoxy-β-enaminals 82-87的產物。3-Deoxy-β-enaminals 82-87的產率為87-95%，伴隨著高度選擇性（E/Z form比率為97:3-98:2）。 β-Enaminals藉由MsCl/pyridine的條件下可合成中等至高產率的C-2-formylglycals，數個問題被深入探討，包括路易士鹼、酸酐（或MsCl）和三號碳及四號碳上取代基之影響。而β-enaminal與imidazole/PPh3/I2反應亦可合成高產率的C-2-formylglycal。 β-Enaminals同樣可以和SOCl2、I2、TMS/LiBr及Ac2O/d-DMSO進行反應，產生非預期的新化合物。 3-Deoxy-β-enaminals 82-87 that had been prepared by Michael addition of 3-deoxy-C-2-formylglycals 80-81 with 1.1 eguiv of primary amine (including benzylamine, n-butylamine and n-octylamine) in MeOH for 10 minutes. The product, 3-deoxy-β-enaminals 82-87 were abtained in 87-95% with high selectivity (ratio of E/Z: 97:3-98:2). C-2-Formylglycals were synthesized in medium to good yield by MsCl/pyridine of β-enaminals. Several issues were addressed in depth, including the effect of Lewis bases, acid anhydrides (or MsCl), and the substutient at C3 and C4 position. C-2-Formylglycal was also synthesized in good yield by treating of β-enaminal with imidazole/PPh3/I2. β-enaminals were also reacted with SOCl2, I2, TMSCl/LiBr, and Ac2O /d-DMSO to produce unexpected new compounds.
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