(((2R,3S)-1,3-bis(benzyloxy)hex-5-en-2-yl)oxy)(tert-butyl)dimethylsilane | 1337989-76-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (((2R,3S)-1,3-bis(benzyloxy)hex-5-en-2-yl)oxy)(tert-butyl)dimethylsilane
• 英文别名: ((2R,3S)-1,3-bis(benzyloxy)hex-5-en-2-yloxy)(tert-butyl)dimethylsilane；[(2R,3S)-1,3-bis(phenylmethoxy)hex-5-en-2-yl]oxy-tert-butyl-dimethylsilane
• CAS: 1337989-76-0
• 化学式: C₂₆H₃₈O₃Si
• 分子量: 426.671
• InChiKey: IZGWXMIJFKGWPV-LOSJGSFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.76
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (((2R,3S)-1,3-bis(benzyloxy)hex-5-en-2-yl)oxy)(tert-butyl)dimethylsilane 在 4-二甲氨基吡啶 、 四氯化钛 、 sodium hydride 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 (S)-(2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-6'-formyl-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazin]-4-yl 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Acortatarins A和B的全合成和立体化学修饰

  摘要：

  通过使用容易获得的d-糖描述了第一步的全合成的角蛋白A，B和对映体结构的对映体。这种聚合的总合成揭示了对阿考塔林A的绝对构型的修订和对阿考塔林B的结构的修订。涉及的关键步骤是用去质子化的2，5-二取代的吡咯进行的区域选择性环氧化物的开环和螺缩酮化。

  DOI：

  10.1021/ol202121k
• 作为产物：
  描述：

  1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 在 2,6-二甲基吡啶 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.5h， 生成 (((2R,3S)-1,3-bis(benzyloxy)hex-5-en-2-yl)oxy)(tert-butyl)dimethylsilane
  参考文献：
  名称：

  Xylapyrrosides A and B, two rare sugar-morpholine spiroketal pyrrole-derived alkaloids from Xylaria nigripes: isolation, complete structure elucidation, and total syntheses

  摘要：

  Two new [named xylapyrrosides A (1) and B (2)1 along with two known [pollenopyrrosides A (3) and B (=acortatarin A, 4)] naturally occurring spirocyclic pyrrole alkaloids were isolated and identified as minor components from the Et0H extract of the dried mycelia of the edible medicinal fungus Xylaria nigripes. Their structures were established by a combination of interpretation of spectroscopic data and single-crystal X-ray diffraction analyses. The isolates possess a unique tricyclic skeleton comprising a common bicyclic 2-formyl-pyrrole-fused morpholine, with a variable ketohexoside ring. This class of alkaloids is quite rare from natural sources. In this study, the total syntheses of compounds 1, 2 and 4 were successfully achieved by two alternative strategies, and three new analogs [named xylapyrrosides A(1) (1a), A(2) (1b) and B-1 (2a)] were also produced. Notably, the total synthesis of such spiroketal alkaloids with a pyranose ring (e.g.,1) was accomplished for the first time. The absolute configurations of the new isolates can be thereafter unequivocally secured by the total syntheses. The above isolated and synthesized spiro-alkaloids were found to show moderate antioxidant effects by preventing the oxidative stress-induced cytotoxicity of A7r5 rat vascular smooth muscle cells (VSMCs). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.020

文献信息

• Total Synthesis and Stereochemical Revision of Acortatarins A and B
  作者：Gangarajula Sudhakar、Vilas D. Kadam、Shruthi Bayya、Gavinolla Pranitha、Bharatam Jagadeesh

  DOI：10.1021/ol202121k

  日期：2011.10.21

  A first total synthesis of acortatarins A, B, and an enantiomer of the proposed structure of acortatarin B is described by using readily available d-sugars. This convergent total synthesis revealed the revision of the absolute configuration of acortatarin A and structural revision of acortatarin B. The key steps involved are regioselective epoxide opening with deprotonated 2,5-disubstituted pyrrole

  通过使用容易获得的d-糖描述了第一步的全合成的角蛋白A，B和对映体结构的对映体。这种聚合的总合成揭示了对阿考塔林A的绝对构型的修订和对阿考塔林B的结构的修订。涉及的关键步骤是用去质子化的2，5-二取代的吡咯进行的区域选择性环氧化物的开环和螺缩酮化。
• Xylapyrrosides A and B, two rare sugar-morpholine spiroketal pyrrole-derived alkaloids from Xylaria nigripes: isolation, complete structure elucidation, and total syntheses
  作者：Ming Li、Juan Xiong、Ya Huang、Li-Jun Wang、Yu Tang、Guo-Xun Yang、Xin-Hua Liu、Bang-Guo Wei、Hui Fan、Yun Zhao、Wen-Zhu Zhai、Jin-Feng Hu

  DOI：10.1016/j.tet.2015.06.020

  日期：2015.8

  Two new [named xylapyrrosides A (1) and B (2)1 along with two known [pollenopyrrosides A (3) and B (=acortatarin A, 4)] naturally occurring spirocyclic pyrrole alkaloids were isolated and identified as minor components from the Et0H extract of the dried mycelia of the edible medicinal fungus Xylaria nigripes. Their structures were established by a combination of interpretation of spectroscopic data and single-crystal X-ray diffraction analyses. The isolates possess a unique tricyclic skeleton comprising a common bicyclic 2-formyl-pyrrole-fused morpholine, with a variable ketohexoside ring. This class of alkaloids is quite rare from natural sources. In this study, the total syntheses of compounds 1, 2 and 4 were successfully achieved by two alternative strategies, and three new analogs [named xylapyrrosides A(1) (1a), A(2) (1b) and B-1 (2a)] were also produced. Notably, the total synthesis of such spiroketal alkaloids with a pyranose ring (e.g.,1) was accomplished for the first time. The absolute configurations of the new isolates can be thereafter unequivocally secured by the total syntheses. The above isolated and synthesized spiro-alkaloids were found to show moderate antioxidant effects by preventing the oxidative stress-induced cytotoxicity of A7r5 rat vascular smooth muscle cells (VSMCs). (C) 2015 Elsevier Ltd. All rights reserved.