（R）-3,4-二氢-2H-吡喃-2-甲醛的合成：在强效腺苷A(2A)和A(3)受体激动剂合成中的应用
Synthesis of (R)-3,4-dihydro-2H-pyran-2-carboxaldehyde: application to the synthesis of potent adenosine A(2A) and A(3) receptor agonist.
作者信息
Jagtap Prakash G, Chen Zhiyu, Koppetsch Karsten, Piro Elizabeth, Fronce Paula, Southan Garry J, Klotz Karl-Norbert
机构信息
Inotek Pharmaceuticals Corporation, 33 Hayden Avenue, Lexington, MA 02421, USA.
出版信息
Tetrahedron Lett. 2009 Jun 3;50(22):2693-2696. doi: 10.1016/j.tetlet.2009.03.148.
Abstract
Synthesis of potent adenosine A(2A) and A(3) receptor agonist from the modification of adenosine-5'-N-ethylcarboxamide (NECA) has been reported. Diastereoisomer possessing an (R) 3,4-dihydro-2H-pyranyl (DHP) moiety exhibited the highest affinity at the A(2A) and A(3) receptors. The key steps involve the synthesis of (R)-3,4-dihydro-2H-pyran-2-carboxaldehyde (7), which was obtained through the enzyme catalyzed kinetic resolution of (±)-2-acetoxymethyl-3,4-dihydro-2H-pyran (5).
摘要
据报道，通过对腺苷-5'-N-乙基甲酰胺（NECA）进行修饰合成了强效腺苷A(2A)和A(3)受体激动剂。具有(R) 3,4-二氢-2H-吡喃基（DHP）部分的非对映异构体在A(2A)和A(3)受体上表现出最高亲和力。关键步骤包括(R)-3,4-二氢-2H-吡喃-2-甲醛（7）的合成，它是通过(±)-2-乙酰氧基甲基-3,4-二氢-2H-吡喃（5）的酶催化动力学拆分得到的。
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