(8S,8aR)-8-(t-butyldimethylsilyloxy)-8,8a-dihydro-1H-oxazolo[3,4-a]pyridin-3(5H)-one | 220784-94-1

• 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: (8S,8aR)-8-(t-butyldimethylsilyloxy)-8,8a-dihydro-1H-oxazolo[3,4-a]pyridin-3(5H)-one
• 英文别名: (8S,8aR)-8-[tert-butyl(dimethyl)silyl]oxy-1,5,8,8a-tetrahydro-[1,3]oxazolo[3,4-a]pyridin-3-one
• CAS: 220784-94-1
• 化学式: C₁₃H₂₃NO₃Si
• 分子量: 269.416
• InChiKey: YDMPNIJAIGSRGR-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8S,8aR)-8-(t-butyldimethylsilyloxy)-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 、 水 、 4-甲基苯磺酸吡啶 作用下， 以 丙酮 、 叔丁醇 为溶剂， 反应 28.0h， 生成 1-脱氧甘露伊霉素
  参考文献：
  名称：

  New entry for asymmetric deoxyazasugar synthesis: syntheses of deoxymannojirimycin, deoxyaltrojirimycin and deoxygalactostatin

  摘要：

  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。

  DOI：

  10.1039/a807532h
• 作为产物：
  描述：

  (8S,8aS)-8-hydroxy-8,8a-dihydro-1H-oxazolo[3,4-a]pyridin-3(5H)-one 在 2,6-二甲基吡啶 、 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 (8S,8aR)-8-(t-butyldimethylsilyloxy)-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。
• 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。
• Practical synthesis of optically active bicyclic oxazolidinylpiperidines, chiral building blocks for preparing 1-deoxyazasugars, from serine
  作者：Masaaki Shirai、Sentaro Okamoto、Fumie Sato

  DOI：10.1016/s0040-4039(99)00969-7

  日期：1999.7

  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.