(6S,7R,8S,8aS)-octahydroindolizine-6,7,8-triol | 141116-90-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (6S,7R,8S,8aS)-octahydroindolizine-6,7,8-triol
• 英文别名: (6S,7R,8S,8aS)-6,7,8-Trihydroxyindolizidine；1-Deoxy-8,8a-di-epi-castanospermine；1-deoxy-8,8a-diepicastanospermine；(6S,7R,8S,8aS)-1,2,3,5,6,7,8,8a-octahydroindolizine-6,7,8-triol
• CAS: 141116-90-7
• 化学式: C₈H₁₅NO₃
• 分子量: 173.212
• InChiKey: NCQXPGNMJJWGLP-DKXJUACHSA-N

物化性质

• 熔点：
  157-159 °C
• 沸点：
  353.3±31.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  63.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2S)-N-苄氧羰基-2-吡咯烷甲醛 在 四氯化碳 、 sodium hydroxide 、 四氧化锇 、 camphor-10-sulfonic acid 、 水 、 potassium carbonate 、 N-甲基吗啉氧化物 、 间氯过氧苯甲酸 、 三苯基膦 、 三氟乙酸 、 三甲氧基磷 作用下， 以 甲醇 、 二氯甲烷 、 水 、 异丙醇 、 丙酮 、 叔丁醇 为溶剂， 反应 113.0h， 生成 (6S,7R,8S,8aS)-octahydroindolizine-6,7,8-triol
  参考文献：
  名称：

  Synthesis of 1-deoxycastanospermine and stereoisomers

  摘要：

  Four different isomers of 1-deoxycastanospermine (6,7,8-trihydroxyindolizidine) were synthesized. Their basic skeleton was constructed from a proline derivative and the anion of allyl phenyl sulfide, followed by an allylic sulfide rearrangement and a subsequent nucleophilic cyclization. The aminotriols were obtained in good yields with a concise overall sequence.

  DOI：

  10.1021/jo00037a025

文献信息

• Synthesis of trihydroxylated pyrrolizidine and indolizidine alkaloids based on SmI2-induced reductive coupling of chiral nitrones with methyl acrylate
  作者：Juraj Rehák、Lubor Fišera、Jozef Kožíšek、Lenka Bellovičová

  DOI：10.1016/j.tet.2011.05.129

  日期：2011.8

  Synthesis of trihydroxylated pyrrolizidines, the enantiomer of 2-epihyacinthacine A2 and indolizidine analogues of the natural alkaloids is reported. The key step of these syntheses is the stereoselective samarium diodide-induced coupling of the chiral nitrone prepared from d-ribose with methyl acrylate. The nitrone derived from d-ribose possessing C2/C3 syn configuration reacted with methyl acrylate

  据报道，合成了三羟基化的吡咯嗪核苷，2-表庚氨酸A 2的对映异构体和天然生物碱的吲哚并嗪类似物。这些合成的关键步骤是立体选择性二碘化mar诱导的由d-核糖与丙烯酸甲酯制备的手性硝酮的偶联。在二碘化sa存在下，具有C2 / C3顺式构型的d-核糖衍生的硝酮与丙烯酸甲酯反应，具有极好的收率和非对映选择性，仅检测到抗-非对映异构体。
• Polyhydroxylated indolizidine alkaloids—an efficient synthesis of 1-deoxy-8,8a-di-epi-castanospermine
  作者：Ari M.P Koskinen、Oili A Kallatsa

  DOI：10.1016/s0040-4020(03)00918-9

  日期：2003.8

  on amino acid and β-ketophosphonate chemistry, as well as employment of internal asymmetric induction for the creation of the new chiral centers proved successful. With proper choice of reaction conditions, the approach can also be applied in selective preparation of several isomers of deoxycastanospermine. The length (9 steps) and overall yield of the title compound trihydroxyindolidine 1, 7.3%, compares

  基于氨基酸和β-酮膦酸酯化学，开发了一种新的有效的对映选择性全合成标题脱氧卡那精胺衍生物，并证明内部不对称诱导用于创建新的手性中心是成功的。随着反应条件的适当选择，该方法也可以在deoxycastanospermine的多种异构体的选择性制备施用。标题化合物三羟基吲哚啶1的长度（9步）和总产率为7.3％，与相似化合物的文献合成相比较。
• α,β-Unsaturated Diazoketones as Platforms in the Asymmetric Synthesis of Hydroxylated Alkaloids. Total Synthesis of 1-Deoxy-8,8a-diepicastanospermine and 1,6-Dideoxyepicastanospermine and Formal Synthesis of Pumiliotoxin 251D
  作者：Barbara Bernardim、Vagner D. Pinho、Antonio C. B. Burtoloso

  DOI：10.1021/jo301967w

  日期：2012.11.2

  A versatile and concise approach for the stereoselective synthesis of mono-, di-, and trihydroxylated indolizidines is presented in four to six steps from Cbz-prolinal and a diazophosphonate. The key steps involved a Wolff rearrangement, followed by a stereoselective dihydroxylation/epoxidation reaction, from an α,β-unsaturated diazoketone. The strategy also permits extension to the synthesis of many

  从Cbz-脯氨酸和重氮膦酸酯的四至六个步骤中提出了一种立体选择性合成单羟基，二羟基和三羟基吲哚并吡啶的通用且简洁的方法。关键步骤涉及沃尔夫夫重排，然后是来自α，β-不饱和重氮酮的立体选择性二羟基化/环氧化反应。该策略还允许扩展到许多天然羟基化的吲哚并立定生物碱的合成，如pumiliotoxin 251D的正式合成所证明的。
• Asymmetric Synthesis of 1-Deoxy-8,8a-di-epi-castanospermine
  作者：Stephen F. Martin、Hui-Ju Chen、Vincent M. Lynch

  DOI：10.1021/jo00106a051

  日期：1995.1
• Synthesis of 1-deoxycastanospermine and stereoisomers
  作者：Yves St-Denis、Tak Hang Chan

  DOI：10.1021/jo00037a025

  日期：1992.5

  Four different isomers of 1-deoxycastanospermine (6,7,8-trihydroxyindolizidine) were synthesized. Their basic skeleton was constructed from a proline derivative and the anion of allyl phenyl sulfide, followed by an allylic sulfide rearrangement and a subsequent nucleophilic cyclization. The aminotriols were obtained in good yields with a concise overall sequence.