(6S,7R,8R,8aS)-6,7,8-trihydroxy-indolizidine | 141116-92-9

• 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,8R,8aS)-6,7,8-trihydroxy-indolizidine
• 英文别名: (6S,7R,8R,8aS)-6,7,8-Trihydroxyindolizidine；1-deoxy-8a-epi-castanospermine；1-Deoxy-8a-epicastanospermine；8a-epi-1-deoxycastanospermine；(6S,7R,8R,8aS)-1,2,3,5,6,7,8,8a-octahydroindolizine-6,7,8-triol
• CAS: 141116-92-9
• 化学式: C₈H₁₅NO₃
• 分子量: 173.212
• InChiKey: NCQXPGNMJJWGLP-RULNZFCNSA-N

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,8R,8aS)-6,7,8-trihydroxy-indolizidine
  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

• A new synthetic access to bicyclic polyhydroxylated alkaloid analogues from pyranosides
  作者：Ning Wang、Li-He Zhang、Xin-Shan Ye

  DOI：10.1039/b923180c

  日期：——

  A facile, versatile and stereoselective synthesis of bicyclic polyhydroxylated alkaloids as castanospermine analogues is described. The synthetic route started from methyl pyranosides. The key steps involved a high-yielding expeditious one-pot tandem reaction from alkenes to N-substituted δ-lactams. The δ-lactams were stereoselectively vinylated to give the dienes, which were followed by the ring-closing

  一种简便，通用和立体选择性的双环多羟基化生物碱的合成方法 粟精胺描述了类似物。合成途径从甲基吡喃糖苷开始。关键步骤涉及从烯烃到高产率的快速一锅串联反应ñ取代的δ-内酰胺。δ-内酰胺经立体选择性乙烯基化得到二烯，然后进行闭环复分解反应生成环化产物。所得双环化合物的官能团转化以良好的产率提供了多种多羟基化生物碱。
• The 5-Endo-trig Cyclization of D-Glucose Derived γ-Alkenylamines with Mercury (II) Salts: Synthesis of 1-Deoxycastanospermine and its 8a-epi-Analogue†
  作者：D. Dhavale、S. Jachak

  DOI：10.3390/10080893

  日期：——

  The intramolecular aminomercuration of γ-alkenylamines 1a, 1b and 4 was shown to afford the 5-endo-trig cyclized product exclusively in good yield. The utility of pyrrolidine derivatives thus obtained from D-glucose derived γ-alkenylamines 1a and 1b was demonstrated in the synthesis of 1-deoxycastanospermine (3a) and 1-deoxy-8a-epi-castanospermine (3b).

  γ-链烯基胺 1a、1b 和 4 的分子内氨基汞化显示仅以良好的产率提供 5-endo-trig 环化产物。由此从 D-葡萄糖衍生的 γ-链烯基胺 1a 和 1b 获得的吡咯烷衍生物的效用在 1-脱氧栗精胺 (3a) 和 1-脱氧-8a-epi-栗精胺 (3b) 的合成中得到证明。
• Intermolecular Michael Addition of Substituted Amines to a Sugar-Derived α,β-Unsaturated Ester:  Synthesis of 1-Deoxy-<scp>d</scp>-<i>g</i><i>luco</i>- and -<scp>l</scp>-<i>i</i><i>do</i>-homonojirimycin, 1-Deoxy-castanospermine and 1-Deoxy-8a-<i>epi</i>-castanospermine
  作者：Nitin T. Patil、Jayant N. Tilekar、Dilip D. Dhavale

  DOI：10.1021/jo0010476

  日期：2001.2.1

  The synthesis of polyhydroxylated piperidine alkaloids, namely, 1-deoxy-D-gluco-homonojirimycin 3a, 1-deoxy-L-ido-homonojirimycin 3b, and indolizidine alkaloids 1-deoxy-castanospermine 5a and 1-deoxy-8a-epi-castanospermine 5b, has been achieved. The key step involved is the intermolecular Michael addition of benzylamine to alpha,beta-unsaturated ester 1, derived from D-glucose, which afforded diastereomeric

  多羟基化哌啶生物碱的合成，即1-脱氧-D-葡萄糖-homonojirimycin 3a，1-deoxy-L-ido-homonojirimycin 3b和吲哚并立生物碱1-deoxy-castanospermine 5a和1-deoxy-8a-ep-castanospermine 5b，已经实现。涉及的关键步骤是将分子胺在分子间的Michael加成反应中衍生自D-葡萄糖的α，β-不饱和酯1，从而得到β-氨基酯6a和6b的非对映异构体混合物，其中D-葡萄糖和L-ido-构型为C5分别。尝试增加和/或改变新生成的立体中心的非对映选择性。通过使用N-苄基氨基化锂作为迈克尔供体，在动力学控制的条件下实现了有利于L-偶合异构体6b的高立体选择性。β-氨基酯6a和6b代表目标分子的常见中间体。因此，LAH分别减少6a和6b，得到β-氨基醇7a和7b。依次氢解，氨基的选择性保护，然后水解1，2-丙酮化物
• Contribution to the synthesis of polyhydroxylated indolizidines starting from sugar isothiocyanates
  作者：Ján Elečko、Jozef Gonda、Miroslava Martinková、Mária Vilková

  DOI：10.1016/j.tetasy.2016.02.011

  日期：2016.5
• A short and efficient synthesis of 1-deoxy-castanospermine and 1-deoxy-8a-epi-castanospermine
  作者：Nitin T Patil、Jayant N Tilekar、Dilip D Dhavale

  DOI：10.1016/s0040-4039(00)02103-1

  日期：2001.1

  A new route for the synthesis of 1-deoxy-castanospermine 2 and 1-deoxy-8a-epi-castanospermine 3 has been developed via a sequential triple reductive amination process of a suitably protected D-gluco-oct-5-ulo-1,8-dialdose, which was easily prepared by three carbon homologation of readily available alpha -D-xylo-pentodialdose using an appropriate Grignard reagent followed by oxidation. (C) 2001 Elsevier Science Ltd. All rights reserved.