(1S,2R,8R,8aR)-8-hydroxy-1,2-(isopropylidenedioxy)octahydroindolizin-5-one | 107080-62-6

• 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: (1S,2R,8R,8aR)-8-hydroxy-1,2-(isopropylidenedioxy)octahydroindolizin-5-one
• 英文别名: (1S,2R,8R,8aR)-1,2-isopropylidenedioxy-8-hydroxy-octahydro-5-indolizinone；(1S,2R,8R,8aR)-8-hydroxy-1,2-(isopropylidenedioxy)indolizidin-5-one；(3aR,9R,9aR,9bS)-9-hydroxy-2,2-dimethyl-4,7,8,9,9a,9b-hexahydro-3aH-[1,3]dioxolo[4,5-a]indolizin-6-one
• CAS: 107080-62-6；127420-72-8；98362-03-9
• 化学式: C₁₁H₁₇NO₄
• 分子量: 227.26
• InChiKey: NGTBXJRLBRIVQS-KHUVANEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R,8R,8aR)-8-hydroxy-1,2-(isopropylidenedioxy)octahydroindolizin-5-one 在 二甲基硫 、 硼烷 、 三氟乙酸 作用下， 生成 八倾吲嗪三醇
  参考文献：
  名称：

  甘露糖苷酶抑制剂swainsonine和1,4-dideoxy-1,4-imino-D-甘露醇的合成以及环收缩的swainsonines（1S，2R，7R，7aR）-1,2,7-三羟基吡咯烷并（1S， 2R，7S，7aR）-1,2,7-三羟基吡咯烷

  摘要：

  4,5-脱水-1-叠氮基-1-脱氧-2,3-O-异亚丙基-D-塔罗糖醇是一种高效有效合成1,4-二脱氧-1,4-亚氨基-D-的异体中间体甘露醇，swainsonine和环收缩的swainsonines中的（1S，2R，7R，7aR）-1,2,7-三羟基吡咯烷并（1S，2R，7S，7aR）-1,2,7-三羟基吡咯烷并。据报道，收缩的swainsonines对糖苷酶的作用。

  DOI：

  10.1016/s0040-4039(01)93953-x
• 作为产物：
  描述：

  (R)-1-((4R,5S)-5-((S)-1-hydroxyallyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol 在 palladium dihydroxide 、 potassium osmate(VI) 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 sodium periodate 、 甲基磺酰胺 、 ammonium formate 、 silica gel 、 sodium cyanoborohydride 、 potassium carbonate 、 溶剂黄146 、 丙酸 、 三乙胺 、 potassium hexacyanoferrate(III) 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 174.5h， 生成 (1S,2R,8R,8aR)-8-hydroxy-1,2-(isopropylidenedioxy)octahydroindolizin-5-one
  参考文献：
  名称：

  A Synthesis of (1S,2R,8R,8aR)-8-Hy- droxy-1,2-(isopropylidinedioxy)indolizidin-5-one from D-Ribose: Improved Access to (-)-Swainsonine and Its Analogs

  摘要：

  DOI：

  10.3987/com-02-s(m)40

文献信息

• An enantiocontrolled synthesis of (−)-swainsonine
  作者：Sung Ho Kang、Geun Tae Kim

  DOI：10.1016/0040-4039(95)00920-8

  日期：1995.7

  (−)-Swainsonine 1, first isolated from the fungus Rhizoctonia leguminicola, has been sythesized enantioseletively. The key step was the stereoselective iodoamination of trichloro- acetimidate derived from (Z)-olefinic allylic alcohol 7.

  （-）-Swainsonine 1，首先从真菌Rhizoctonia leguminicola中分离出来，已被对映体合成。关键步骤是衍生自（Z）-烯烃烯丙醇7的三氯乙酰亚胺的立体选择性碘胺化。
• Concise and divergent total synthesis of swainsonine, 7-alkyl swainsonines, and 2,8a-diepilentiginosine via a chiral heterocyclic enaminoester intermediate
  作者：Gao-Feng Shi、Jia-Qi Li、Xiao-Ping Jiang、Ying Cheng

  DOI：10.1016/j.tet.2008.03.080

  日期：2008.5

  The concise and divergent total syntheses of (−)-swainsonine, (−)-7-alkyl swainsonines, and (−)-2,8a-diepilentiginosine from a common chiral heterocyclic enaminoester intermediate in five-step sequences are presented. The highly efficient annulation reaction of the chiral heterocyclic enaminoester with various α,β-unsaturated carboxylates, and a straightforward carboxy inversion constituted the key

  从五个步骤序列中，从一个常见的手性杂环烯胺酯中间体中得出了（-）-swainsonine，（-）-7-烷基swainsonines和（-）-2,8a-dipilentiginosine的简明和不同的总合成物。手性杂环烯胺酸酯与各种α，β-不饱和羧酸酯的高效环合反应以及直接的羧基转化是合成途径的关键特征。这项工作为从容易获得的平台不同合成不同的天然和非天然多羟基吲哚并吡啶类化合物提供了一个实例。
• A concise synthetic method towards (−)-swainsonine and its 8-epimer by using palladium-catalyzed asymmetric hydroamination of alkoxyallene as the key strategy
  作者：Wontaeck Lim、Young Ho Rhee

  DOI：10.1016/j.tet.2015.05.034

  日期：2015.9

  hydroamination of alkoxyallene and the Ru-catalyzed ring-closing-metathesis as the key strategy, which generates cyclic allylic N,O-acetal as the pivotal intermediate. Notably, this reaction could be performed on a multigram-scale. In addition, both the natural product and its 8-epimer could be obtained with comparable synthetic efficiency.

  报告了（-）-swainsonine和8-epimer的简洁灵活的形式合成方法。合成过程以Pd顺序催化烷氧基丙二烯不对称加氢胺化和Ru催化的闭环复分解为关键策略，生成环状烯丙基N，O-缩醛作为关键中间体。值得注意的是，该反应可以在数克规模上进行。另外，天然产物及其8-末端异构体都可以以相当的合成效率获得。
• Preparation of immobilized swainsonine analogs on solid support
  作者：William H Pearson、Luyi Guo、Tanya M Jewell

  DOI：10.1016/s0040-4039(02)00254-x

  日期：2002.3

  Golgi alpha-mannosidase II and lysosomal mannosidase are examples of biologically important alpha-mannosidases that are difficult to purify. Swainsonine is an effective inhibitor of these a-mannosidases. In this report, analogs of swainsonine bearing an aminoalkyl group at C3 or C6 are synthesized and coupled with AM-Gel 10 to prepare affinity matrices that may be useful for the preparation of alpha-mannosidases. Model ligands, where the aminoalkyl group is capped with an acyl group, are evaluated against a commercial alpha-mannosidase. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Honda, Toshio; Hoshi, Michiyasu; Kanai, Kazuo, Journal of the Chemical Society. Perkin transactions I, 1994, # 15, p. 2091 - 2102
  作者：Honda, Toshio、Hoshi, Michiyasu、Kanai, Kazuo、Tsubuki, Masayoshi

  DOI：——

  日期：——