(8R,8aS)-8-hydroxy-8,8a-dihydro-1H-oxazolo[3,4-a]pyridin-3(5H)-one | 241491-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (8R,8aS)-8-hydroxy-8,8a-dihydro-1H-oxazolo[3,4-a]pyridin-3(5H)-one
• 英文别名: (8S,8aR)-8-hydroxy-1,5,8,8a-tetrahydrooxazolo[3,4-a]pyridin-3-one；(8S,8aR)-8-hydroxy-1,5,8,8a-tetrahydro-[1,3]oxazolo[3,4-a]pyridin-3-one
• CAS: 241491-22-5
• 化学式: C₇H₉NO₃
• 分子量: 155.153
• InChiKey: HGLFTKVZIXIWEB-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8R,8aS)-8-hydroxy-8,8a-dihydro-1H-oxazolo[3,4-a]pyridin-3(5H)-one 在 盐酸 、 sodium hydroxide 、 四氧化锇 、 N-甲基吲哚酮 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 35.0h， 生成 1-甘露糖野尻霉素盐酸盐
  参考文献：
  名称：

  General Approach to Glycosidase Inhibitors. Enantioselective Synthesis of Deoxymannojirimycin and Swainsonine

  摘要：

  Deoxymannojirimycin (2) and swainsonine (4) have been synthesized from each enantiomer of the same bicyclic carbamate precursor 7. The key intermediate was prepared by a simple and efficient three-step synthesis involving RCM of the diene 8, which in turn is easily accessible in any configuration from enantiomerically enriched 2,3-epoxy-4-penten-1-ol 9.

  DOI：

  10.1021/jo048172s
• 作为产物：
  描述：

  (8S,8aS)-8-hydroxy-8,8a-dihydro-1H-oxazolo[3,4-a]pyridin-3(5H)-one 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (8R,8aS)-8-hydroxy-8,8a-dihydro-1H-oxazolo[3,4-a]pyridin-3(5H)-one
  参考文献：
  名称：

  实用合成的光学活性双环恶唑烷二基哌啶，手性构建基，可从丝氨酸制备1-脱氧天竺葵

  摘要：

  Optically active bicyclic oxazolidinylpiperidines 1a, 1b, 1c and 1d, known chiral building blocks for preparing 1-deoxyazasugars, were synthesized in high overall yield from D-serine by a method wherein the titanium(II)-mediated intramolecular nucleophilic acyl substitution and FeCl3-mediated ring enlargement of bicyclic cyclopropanols are the key reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00969-7

文献信息

• A Concise Enantioselective Entry to the Synthesis of Deoxy-azasugars
  作者：Rubén Martín、Albert Moyano、Miquel A. Pericàs、Antoni Riera

  DOI：10.1021/ol991280u

  日期：2000.1.1

  [reaction: see text] A concise enantioselective preparation of oxazolidinylpiperidine 4, a key intermediate in the synthesis of glycosidase inhibitors such as 1-deoxymannojirimycin or 1-deoxygalactostatin, has been developed. Sharpless catalytic asymmetric epoxidation of (E)-2,4-pentadienol followed by treatment with allyl isocyanate afforded epoxy carbamate 8. Regioselective intramolecular ring opening

  [反应：见正文]已经开发了一种简洁的对映体选择性的恶唑烷二基哌啶4，它是合成糖苷酶抑制剂（如1-deoxymannojirimycin或1-deoxygalactostatin）的关键中间体。（E）-2,4-戊二烯醇的无尖锐催化不对称环氧化，然后用异氰酸烯丙酯处理，得到环氧氨基甲酸酯8。由双（三甲基甲硅烷基）酰胺钠促进的区域选择性分子内开环和闭环复分解提供了高对映体的双环中间体4纯度。这四个步骤的顺序总收率为51％。
• Asymmetric synthesis of 1-deoxyazasugars from chiral aziridines
  作者：Alok Singh、Bongchan Kim、Won Koo Lee、Hyun-Joon Ha

  DOI：10.1039/c0ob00730g

  日期：——

  A general and facile synthesis of enantiopure 1-deoxyazasugars was achieved from stereoselective dihydroxylation of a common synthetic intermediate, piperidine ring fused oxazolidin-2-one, originating from a commercially available starting substrate, chiral aziridine-2-carboxylate, in high yields.

  对映体纯的1-脱氧天竺葵的一般和容易的合成是通过常见的合成中间体哌啶环稠合的立体选择性二羟基化而实现的 恶唑烷-2-酮源于可商购的起始底物手性氮丙啶-2-羧酸的手性化合物，收率高。
• Stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc) and ureido-DNJNAc derivatives as new hexosaminidase inhibitors
  作者：Alex de la Fuente、Teresa Mena-Barragán、Ronald A. Farrar-Tobar、Xavier Verdaguer、José M. García Fernández、Carmen Ortiz Mellet、Antoni Riera

  DOI：10.1039/c5ob00507h

  日期：——

  2-Acetamido-1,2-dideoxyiminosugars are selective and potent inhibitors of hexosaminidases and therefore show high therapeutic potential for the treatment of various diseases, including several lysosomal storage disorders. A stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc), the iminosugar analog of N-acetylglucosamine, with a high overall yield is here described. This novel procedure

  2-乙酰氨基-1,2-二脱氧亚氨基糖是己糖胺酶的选择性和有效抑制剂，因此显示出用于治疗多种疾病（包括几种溶酶体贮积症）的高治疗潜力。本文描述了具有高总收率的2-乙酰氨基-1,2-二脱氧野oji霉素（DNJNAc）（N-乙酰氨基葡糖的亚氨基糖类似物）的立体选择性合成。该新方法还允许通过关键关键中间体上的内环胺衍生化获得脲基-DNJNAc共轭物。值得注意的是，某些脲基-DNJNAc代表可作为β-己糖胺酶的有效抑制剂和选择性抑制剂，包括人类酶，是中性sp 2的首例。-亚氨基糖型抑制剂报道了这些酶。此外，新的脲基-DNJNAc的两亲特性有望带来更好的药物样特性。
• Synthesis of oxazolidinyl azacycles via ring-closing olefin metathesis: a practical entry to the synthesis of deoxy-azasugars and hydroxypyrrolizidines
  作者：Thangaiah Subramanian、Chang-Ching Lin、Chun-Cheng Lin

  DOI：10.1016/s0040-4039(01)00635-9

  日期：2001.6

  l-serines, an expedient method for the preparation of oxazolidinyl piperidines, azepenes and azacyclooctenes was illustrated as a route to various deoxy-azasugars and hydroxypyrrolizidines. The ring-closing olefin metathesis of oxazolidinyl di-olefins was used as a key-step to construct the azacycles. Consecutive epoxidation, hydrolysis and transannulation of oxazolidinyl azacyclooctene led to hydroxypyrrolizidines

  从d-和l-丝氨酸开始，说明了一种制备恶唑烷二基哌啶，氮杂环庚烷和氮杂环辛烯的简便方法，作为通往各种脱氧天竺葵和羟基吡咯烷核苷的途径。恶唑烷基二烯烃的闭环烯烃复分解用作构建氮杂环的关键步骤。恶唑烷二基氮杂环辛烯的连续环氧化，水解和环过环生成羟基吡咯烷核苷。
• New entry for asymmetric deoxyazasugar synthesis: syntheses of deoxymannojirimycin, deoxyaltrojirimycin and deoxygalactostatin
  作者：Koji Asano、Toshikazu Hakogi、Seiji Iwama、Shigeo Katsumura

  DOI：10.1039/a807532h

  日期：——

  Deoxyazasugars such as deoxymannojirimycin, deoxyaltrojirimycin and deoxygalactostatin were stereoselectively synthesized starting from (R)-(+)-4-methoxycarbonyloxazolidinone via a bicyclic oxazolidinylpiperidine as a common synthetic intermediate.

  脱氧氨基糖如脱氧甘露糖霉素、脱氧阿洛糖霉素和脱氧半乳糖肽是从(R)-(+)-4-甲氧基羧基氧杂唑烷酮出发，通过一个双环氧杂唑烷基哌啶作为共同的合成中间体进行立体选择性合成的。