(3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-benzyloxymethyl-2-oxohexahydrofuro[2,3-b]pyran | 1124225-72-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: (3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-benzyloxymethyl-2-oxohexahydrofuro[2,3-b]pyran
• 英文别名: (3aR,4R,5S,6R,7aR)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-3,3a,4,5,6,7a-hexahydrofuro[2,3-b]pyran-2-one
• CAS: 1124225-72-4
• 化学式: C₂₉H₃₀O₆
• 分子量: 474.554
• InChiKey: HPNPVSQIIAHDDS-AGVYLGOGSA-N

物化性质

• 熔点：
  87-89 °C
• 沸点：
  630.4±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-benzyloxymethyl-2-oxohexahydrofuro[2,3-b]pyran 在 双(三甲基硅烷基)氨基钾 、 2,4,6-三异丙基苯磺酰叠氮化物 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以88%的产率得到(3S,3aR,4R,5S,6R,7aR)-3-azido-4,5-bis(benzyloxy)-6-benzyloxymethyl-2-oxohexahydrofuro[2,3-b]pyran
  参考文献：
  名称：

  Stereodivergent syntheses at the glucose backbone

  摘要：

  两种具有不同官能团的2-C支化碳水化合物的立体异构体可以从相同的丙二酸酯前体中以良好的产率选择性地得到，仅需要几个步骤。

  DOI：

  10.1039/b918893m
• 作为产物：
  描述：

  methyl 3,4,6-tri-O-benzyl-2-deoxy-2-C-[(dicarboxy)methyl]-β-D-glucopyranoside 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 (3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-benzyloxymethyl-2-oxohexahydrofuro[2,3-b]pyran
  参考文献：
  名称：

  双环碳水化合物1,2-内酯的便捷合成及其对1功能化葡萄糖衍生物的立体选择性开放

  摘要：

  关闭并重新营业：C-2分支碳水化合物1在脱羧条件下以高收率环化为迄今未知的碳水化合物1,2-内酯2。的葡糖异构体可以在异头位置与各种nuceophiles在钪（OTF）的存在下被打开3，这允许1官能化的葡萄糖衍生物的立体选择性合成3。因此，从糖基开始仅需几个步骤即可获得1,2 -bis-C支链糖。

  DOI：

  10.1002/chem.200802178

文献信息

• Stereoselective diversity-oriented syntheses of functionalized saccharides from bicyclic carbohydrate 1,2-lactones
  作者：Jian Yin、Torsten Linker

  DOI：10.1016/j.tet.2011.01.069

  日期：2011.4

  Bicyclic carbohydrate 1,2-lactones have been synthesized in only two steps and high yields by saponification and subsequent cyclization from known malonate addition products to glycals. The gluco-configured lactone serves as an important precursor for diversity-oriented syntheses. Thus, stereoselective opening of the lactone ring was realized with various nucleophiles in the presence of Sc(OTf)(3). This enabled the introduction of different substituents at the anomeric position, to afford a broad variety of 1-functionalized carbohydrates. On the other hand, stereoselective alpha-substitution of the gluco-configured lactone with different electrophiles and subsequent ring opening gives a collection of 2-functionalized saccharides. More than 30 products have been isolated in analytically pure form, and their configurations were unequivocally established by various NMR methods. Thus, carbohydrate 1,2-lactones are attractive precursors for the stereoselective synthesis of diverse saccharides. (C) 2011 Elsevier Ltd. All rights reserved.
• Highly Regio- and Stereoselective One-Pot Synthesis of Carbohydrate-Based Butyrolactones
  作者：Syed Khalid Yousuf、Debaraj Mukherjee、Mallikharjunrao L、Subhash C. Taneja

  DOI：10.1021/ol102723c

  日期：2011.2.18

  The use of manganese(III) acetate allows the direct synthesis of diverse arrays of [4.3.0] bicyclic carbohydrate-based gamma-lactone building blocks from glycals. A mechanism to explain the high regio- and stereoselectivity is proposed. The new reaction has the potential to generate libraries for biological screening.
• Convenient Synthesis of Bicyclic Carbohydrate 1,2-Lactones and Their Stereoselective Opening to 1-Functionalized Glucose Derivatives
  作者：Jian Yin、Torsten Linker

  DOI：10.1002/chem.200802178

  日期：2009.1

  C‐2 branched carbohydrates 1 cyclize under conditions of decarboxylation to the hitherto unknown carbohydrate 1,2‐lactones 2 in high yields. The gluco isomer can be opened at the anomeric position with various nuceophiles in the presence of Sc(OTf)3, which allows the stereoselective synthesis of 1‐functionalized glucose derivatives 3. Thus, 1,2‐bis‐C‐branched saccharides become available in only a few

  关闭并重新营业：C-2分支碳水化合物1在脱羧条件下以高收率环化为迄今未知的碳水化合物1,2-内酯2。的葡糖异构体可以在异头位置与各种nuceophiles在钪（OTF）的存在下被打开3，这允许1官能化的葡萄糖衍生物的立体选择性合成3。因此，从糖基开始仅需几个步骤即可获得1,2 -bis-C支链糖。
• Stereodivergent syntheses at the glucose backbone
  作者：Jian Yin、Torsten Linker

  DOI：10.1039/b918893m

  日期：——

  Both diastereomers of 2-C-branched carbohydrates with various functional groups are selectively available from the same malonate precursor in good yields in only a few steps.

  两种具有不同官能团的2-C支化碳水化合物的立体异构体可以从相同的丙二酸酯前体中以良好的产率选择性地得到，仅需要几个步骤。