methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-formyl-α-D-erythro-hex-2-enopyranoside | 193271-74-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-formyl-α-D-erythro-hex-2-enopyranoside
• 英文别名: (2R,4aR,6S,8aS)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine-8-carbaldehyde
• CAS: 193271-74-8
• 化学式: C₁₅H₁₆O₅
• 分子量: 276.289
• InChiKey: QWZTUFCVASRHRI-CBBWQLFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-formyl-α-D-erythro-hex-2-enopyranoside 在 sodium chlorite 、 sodium dihydrogenphosphate 、 双氧水 、 lithium perchlorate 作用下， 以 乙醚 、 乙酸乙酯 、 乙腈 、 叔丁醇 为溶剂， 反应 18.0h， 生成 (1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Efficient enantiospecific entry to a highly functionalized cyclopentane building block

  摘要：

  A simple and efficient route has been developed for the synthesis of a polyfunctionalized cyclopentane in enantiomerically pure form. D-Glucose is the source of chirality for this versatile building block and a highly diastereoselective Diels-Alder reaction with cyclopentadiene is the key step. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00225-5
• 作为产物：
  描述：

  methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside 在 4-二甲氨基吡啶 、 lithium perchlorate 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 36.25h， 生成 methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-formyl-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  对戊烷内酯相关的奎宁骨架的对映体特异性方法

  摘要：

  对于戊戊内酯化合物家族的有角稠合的三环系统的对映体纯合成，已经描述了一种新颖的通用方法。D-葡萄糖用作原料，非对映选择性Diels-Alder反应确定了环结的元素。

  DOI：

  10.1016/s0040-4039(97)10370-7

文献信息

• Diels−Alder Reaction of Sugar-Derived Cyclic Dienophiles with Cyclopentadiene. Factors Affecting the Reactivity and Stereoselectivity
  作者：Silvina C. Pellegrinet、Rolando A. Spanevello

  DOI：10.1021/ol005619k

  日期：2000.4.1

  showed a high exo and face selectivity in the Diels-Alder reaction with cyclopentadiene. Structural modifications on the dienophile structure were made, and the outcomes of the cycloaddition reactions were investigated. These results and the spectroscopic data recorded within a series of analogues were used to analyze the factors affecting the reactivity and exo selectivity.

  糖衍生的环状亲二烯物在与环戊二烯的狄尔斯-阿尔德反应中表现出较高的外向选择性和面部选择性。对亲二烯体的结构进行了结构修饰，并研究了环加成反应的结果。这些结果和一系列类似物中记录的光谱数据用于分析影响反应性和外切选择性的因素。
• Experimental and theoretical study of a Diels–Alder reaction between a sugar-derived nitroalkene and cyclopentadiene
  作者：María I. Mangione、Ariel M. Sarotti、Alejandra G. Suárez、Rolando A. Spanevello

  DOI：10.1016/j.carres.2010.12.006

  日期：2011.3

  The Diels-Alder reaction of a pyranose-derived nitroalkene 1 with cyclopentadiene is described, and the unexpected facial selectivity of the cycloaddition is analyzed by a computational study.

  描述了吡喃糖衍生的硝基烯烃1与环戊二烯的Diels-Alder反应，并通过计算研究分析了环加成反应的出乎意料的面部选择性。
• Enantiospecific Approach toward Pentalenolactone
  作者：Sebastián A. Testero、Rolando A. Spanevello

  DOI：10.1021/ol061390i

  日期：2006.8.1

  The enantiospecific assembly of the pentalenolactones' carbon skeleton was achieved in 17 steps and 16% overall yield from methyl alpha-D-glucopyranoside. The synthetic strategy relies on two highly efficient key steps: an exo-diastereoselective Diels-Alder reaction and a nonsymmetric ozonolysis.
• Enantiospecific approach to a quinane skeleton related to pentalenolactones
  作者：Silvina C. Pellegrinet、Rolando A. Spanevello

  DOI：10.1016/s0040-4039(97)10370-7

  日期：1997.12

  A novel and general approach has been delineated for the enantiomerically pure synthesis of the angularly fused tricyclic system of the pentalenolactone family of compounds. D-Glucose is used as starting material and a diasteroselective Diels-Alder reaction sets the elements for the ring junctions.

  对于戊戊内酯化合物家族的有角稠合的三环系统的对映体纯合成，已经描述了一种新颖的通用方法。D-葡萄糖用作原料，非对映选择性Diels-Alder反应确定了环结的元素。
• Efficient enantiospecific entry to a highly functionalized cyclopentane building block
  作者：Silvina C. Pellegrinet、Rolando A. Spanevello

  DOI：10.1016/s0957-4166(97)00225-5

  日期：1997.6

  A simple and efficient route has been developed for the synthesis of a polyfunctionalized cyclopentane in enantiomerically pure form. D-Glucose is the source of chirality for this versatile building block and a highly diastereoselective Diels-Alder reaction with cyclopentadiene is the key step. (C) 1997 Elsevier Science Ltd.