(3aR,4R,5R,6R,7aR)-4,5-bis(benzyloxy)-6-benzyloxymethyl-2-oxohexahydrofuro[2,3-b]pyran | 1124225-74-6

• 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,5R,6R,7aR)-4,5-bis(benzyloxy)-6-benzyloxymethyl-2-oxohexahydrofuro[2,3-b]pyran
• CAS: 1124225-74-6
• 化学式: C₂₉H₃₀O₆
• 分子量: 474.554
• InChiKey: HPNPVSQIIAHDDS-PMCIJNRMSA-N

物化性质

• 熔点：
  81-83 °C
• 沸点：
  630.4±55.0 °C(predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  methyl 3,4,6-tri-O-benzyl-2-deoxy-2-C-[(dicarboxy)methyl]-β-D-galactopyranoside 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 (3aR,4R,5R,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

• Highly Regio- and Stereoselective One-Pot Synthesis of Carbohydrate-Based Butyrolactones
  作者：Syed Khalid Yousuf、Debaraj Mukherjee、L Mallikharjunrao、Subhash C. Taneja

  DOI：10.1021/ol400407z

  日期：2013.6.21

  Revised spectral data and spectra as described above. This material is available free of charge via the Internet at http://pubs.acs.org. This article has not yet been cited by other publications. Revised spectral data and spectra as described above. This material is available free of charge via the Internet at http://pubs.acs.org.

  如上所述修改光谱数据和光谱。可通过Internet（http://pubs.acs.org）免费获得此材料。本文尚未被其他出版物引用。如上所述修改光谱数据和光谱。可通过Internet（http://pubs.acs.org）免费获得此材料。
• 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.