(R)-1-{(4R,5S)-5-[(S)-1-(benzylamino)allyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-(tert-butyldimethylsilyloxy)ethanol | 1332640-34-2

• 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: (R)-1-{(4R,5S)-5-[(S)-1-(benzylamino)allyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-(tert-butyldimethylsilyloxy)ethanol
• 英文别名: (1R)-1-((4R,5S)-5-(1-(benzylamino)allyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(tert-butyl-dimethylsilyloxy)ethanol；(1R)-1-[(4R,5S)-5-[(1S)-1-(benzylamino)prop-2-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[tert-butyl(dimethyl)silyl]oxyethanol
• CAS: 1332640-34-2
• 化学式: C₂₃H₃₉NO₄Si
• 分子量: 421.652
• InChiKey: OBJYUGBFLOVHDK-JSXRDJHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-1-{(4R,5S)-5-[(S)-1-(benzylamino)allyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-(tert-butyldimethylsilyloxy)ethanol 在 sodium tetrahydroborate 、 sodium periodate 、 正丁基锂 、 四丁基氟化铵 、 sodium hydride 、 碳酸氢钠 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 wax 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 9.33h， 生成 (S)-3-benzyl-4-((4S,5R)-2,2-dimethyl-5-((Z)-tetradec-1-enyl)-1,3-dioxolan-4-yl)oxa-zolidin-2-one
  参考文献：
  名称：

  A common and stereoselective strategy for the synthesis of N,O,O,O-tetra-acetyl d-ribo-(2S,3S,4R)-phytosphingosine and 2-epi-jaspine B

  摘要：

  A common and stereoselective strategy for the synthesis of N,O,O,O-tetra-acetyl D-ribo-(2S,3S,4R)-phytosphingosine and 2-epi-jaspine B was achieved by using Grignard addition on N-benzyl sugar lactamine and Wittig olefination as key steps. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.032
• 作为产物：
  描述：

  苄胺 在 magnesium 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 (R)-1-{(4R,5S)-5-[(S)-1-(benzylamino)allyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-(tert-butyldimethylsilyloxy)ethanol
  参考文献：
  名称：

  A common and stereoselective strategy for the synthesis of N,O,O,O-tetra-acetyl d-ribo-(2S,3S,4R)-phytosphingosine and 2-epi-jaspine B

  摘要：

  A common and stereoselective strategy for the synthesis of N,O,O,O-tetra-acetyl D-ribo-(2S,3S,4R)-phytosphingosine and 2-epi-jaspine B was achieved by using Grignard addition on N-benzyl sugar lactamine and Wittig olefination as key steps. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.032

文献信息

• A common approach to the total synthesis of l-1-deoxyallonojirimycin, l-homo-1-deoxyazaallose and triacetyl derivative of 5-epi hyacinthacine A5
  作者：Chinthala Muniraju、Maddimsetti Venkateswara Rao、Anugula Rajender、Batchu Venkateswara Rao

  DOI：10.1016/j.tetlet.2016.03.025

  日期：2016.4

  A common strategy for the synthesis of polyhydroxylated piperidines l-1-deoxyallonojirimycin, l-homo-1-deoxyazaallose and triacetyl derivative of 5-epi hyacinthacine A5 from the readily available d-ribose as a starting material has been described.

  对于多羟基哌啶合成的通用策略升-1- deoxyallonojirimycin，升-homo -1- deoxyazaallose和5-三乙酰衍生物外延hyacinthacine阿5从容易获得的d -核糖为起始原料进行了说明。
• A Divergent and Stereoselective Approach for the Syntheses of Some Polyhydroxylated Indolizidine and Pyrrolizidine Iminosugars
  作者：Anugula Rajender、Jalagam Prasada Rao、Batchu Venkateswara Rao

  DOI：10.1002/ejoc.201201342

  日期：2013.3

  A common, divergent, and efficient approach to the syntheses of (+)-steviamine (9), (–)-1-deoxy-8a-epi-castanospermine (10), (+)-trihydroxyindolizidine (11), (+)-3,7a-di-epi-hyacinthacine A1 (12), and (–)-2-epi-lentiginosine (4) was achieved by starting from D-ribose-derived intermediate 13. The key steps involved in these syntheses are a highly diasteroselective Grignard addition to a ribosylimine

  (+)-steviamine (9), (–)-1-deoxy-8a-epi-castanospermine (10), (+)-trihydroxyindolizidine (11), (+) -3,7a-di-epi-hyacinthacine A1 (12) 和 (-)-2-epi-lentiginosine (4) 是从 D-核糖衍生的中间体 13 开始获得的。这些合成中涉及的关键步骤是核糖亚胺的高度非对映选择性格氏加成、一锅立体选择性分子内还原胺化、甲硅烷基醚的选择性脱保护和闭环复分解 (RCM) 反应。