(3R,4R,5R)-3,4,5-tris(phenylmethoxy)-2,3,4,5-tetrahydropyridine | 1570184-20-1

• 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: (3R,4R,5R)-3,4,5-tris(phenylmethoxy)-2,3,4,5-tetrahydropyridine
• CAS: 1570184-20-1
• 化学式: C₂₆H₂₇NO₃
• 分子量: 401.505
• InChiKey: VTFOZOZOWFBGEC-CYXNTTPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  40
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R)-3,4,5-tris(phenylmethoxy)-2,3,4,5-tetrahydropyridine 、 乙烯基溴化镁 在 ytterbium(III) triflate 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以95%的产率得到
  参考文献：
  名称：

  Sugar-derived cyclic imines: one-pot synthesis and direct functionalization

  摘要：

  A simple method for the synthesis of sugar-derived imines by a Schwartz's reagent reduction of easily available sugar lactams has been described. A direct addition of nucleophiles to the generated in situ cyclic imines and subsequent deprotection of hydroxyl function allows to convert sugar lactams in polyhydroxylated pyrrolidines and piperidines. (C) 2014 Elsevier Ltd. All rights

  DOI：

  10.1016/j.tet.2014.01.039
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-D-lyxono-1,5-lactone 在 三乙基硅烷 、 Schwartz's reagent 、 三氟化硼乙醚 、 氨 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 6.25h， 生成 (3R,4R,5R)-3,4,5-tris(phenylmethoxy)-2,3,4,5-tetrahydropyridine
  参考文献：
  名称：

  Sugar-derived cyclic imines: one-pot synthesis and direct functionalization

  摘要：

  A simple method for the synthesis of sugar-derived imines by a Schwartz's reagent reduction of easily available sugar lactams has been described. A direct addition of nucleophiles to the generated in situ cyclic imines and subsequent deprotection of hydroxyl function allows to convert sugar lactams in polyhydroxylated pyrrolidines and piperidines. (C) 2014 Elsevier Ltd. All rights

  DOI：

  10.1016/j.tet.2014.01.039

文献信息

• Synthesis of Polyhydroxylated Quinolizidine and Indolizidine Scaffolds from Sugar-Derived Lactams via a One-Pot Reduction/Mannich/Michael Sequence
  作者：Piotr Szcześniak、Sebastian Stecko、Elżbieta Maziarz、Olga Staszewska-Krajewska、Bartłomiej Furman

  DOI：10.1021/jo502146z

  日期：2014.11.7

  A direct approach to the synthesis of indolizidine and quinolizidine scaffolds of iminosugars is described. The presented strategy is based on a one-pot sugar lactam reduction with Schwartz’s reagent followed by a diastereoselective Mannich/Michael tandem reaction of the resulting sugar imine with Danishefsky’s diene. The stereochemical course of the investigated reaction has been explained in detail

  描述了一种直接合成亚氨基糖的吲哚并立定和喹喔嗪骨架的方法。提出的策略是基于先用Schwartz试剂还原一锅糖内酰胺，然后再将得到的糖亚胺与Danishefsky的二烯进行非对映选择性的Mannich / Michael串联反应。已详细解释了所研究反应的立体化学过程。所获得的双环产物是用于合成各种天然存在的多羟基化生物碱及其衍生物的有吸引力的结构单元。
• Synthesis of Polyhydroxylated Piperidine and Pyrrolidine Peptidomimetics via One-Pot Sequential Lactam Reduction/Joullié–Ugi Reaction
  作者：Piotr Szcześniak、Elżbieta Maziarz、Sebastian Stecko、Bartłomiej Furman

  DOI：10.1021/acs.joc.5b00335

  日期：2015.4.3

  A direct approach to the synthesis of poly-hydroxylated piperidine and pyrrolidine peptidomimetics is described. The presented strategy is based on one-pot reduction of sugar-derived lactams with Schwartz's reagent followed by a multicomponent Ugi-Joullie reaction.