2,3,4-tri-O-benzyl-D-lyxono-1,5-lactone | 1006590-20-0

• 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: 2,3,4-tri-O-benzyl-D-lyxono-1,5-lactone
• 英文别名: (3S,4S,5R)-3,4,5-tris(phenylmethoxy)oxan-2-one
• CAS: 1006590-20-0
• 化学式: C₂₆H₂₆O₅
• 分子量: 418.489
• InChiKey: FXZASCOMEUCXNB-DSITVLBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 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：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-D-lyxopyranose 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 生成 2,3,4-tri-O-benzyl-D-lyxono-1,5-lactone
  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

• The Effect of Electrostatic Interactions on Conformational Equilibria of Multiply Substituted Tetrahydropyran Oxocarbenium Ions
  作者：Michael T. Yang、K. A. Woerpel

  DOI：10.1021/jo8017846

  日期：2009.1.16

  the conformational preference of the C-5 alkoxymethyl group. Although the monosubstituted C-5 alkoxymethyl substituent preferred a pseudoequatorial orientation, the C-5−C-6 bond rotation was controlled by an electrostatic effect. The preferred diaxial conformer of the trans-4,5-disubstituted tetrahydropyranyl system underscored the importance of electrostatic effects in dictating conformational equilibria

  通过对光谱、计算和反应性数据的分析，确定了与糖基阳离子相关的二氧碳鎓离子的三维结构。二氧碳鎓离子的假设低能量结构与实验确定的两者相关1H NMR 耦合常数和非对映选择性来自亲核取代反应。该方法证实了 C-3 烷氧基取代系统的假轴偏好，并揭示了 C-5 烷氧基甲基的构象偏好。尽管单取代的 C-5 烷氧基甲基取代基优选伪赤道取向，但 C-5-C-6 键旋转受静电效应控制。反式-4,5-二取代四氢吡喃系统的首选双轴构象异构体强调了静电效应在决定构象平衡方面的重要性。在 2-脱氧甘露糖体系中，虽然空间效应影响 C-5 烷氧基甲基取代基的取向，但由于静电稳定，全轴构象异构体受到青睐。
• C-2 Epimerization of aldonolactones promoted by magnesium iodide: a new way towards non-enzymatic epimerization
  作者：Julie Gratien、Marie-Pierre Heck、Charles Mioskowski

  DOI：10.1016/j.carres.2007.10.006

  日期：2008.1

  The first example of a non-enzymatic C-2 epimerization of aldonolactones is reported. The reaction of 2,3,4,6-tetra-O-benzyl-D-gluconolactone or 2,3,4,6-tetra-O-benzyl-D-mannonolactone with MgI2 in EtOH afforded their respective C-2 epimer. Studies conducted in EtOD showing the incorporation of a deuterium atom only at the C-2 position of the epimerized product reveal an epimerization rather than a racemization reaction. A mechanism involving a chelation with a magnesium species is proposed to explain this C-2 inversion reaction. (c) 2007 Elsevier Ltd. All rights reserved.
• Sugar-derived cyclic imines: one-pot synthesis and direct functionalization
  作者：Piotr Szcześniak、Sebastian Stecko、Olga Staszewska-Krajewska、Bartłomiej Furman

  DOI：10.1016/j.tet.2014.01.039

  日期：2014.3

  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