2,5:3,4-dianhydro-1,6-di-O-trityl-D-altritol | 798574-25-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2,5:3,4-dianhydro-1,6-di-O-trityl-D-altritol
• 英文别名: 1,6-di-O-trityl-2,5:3,4-dianhydro-D-allitol；(1R,2R,4R,5S)-2,4-bis(trityloxymethyl)-3,6-dioxabicyclo[3.1.0]hexane
• CAS: 798574-25-1
• 化学式: C₄₄H₃₈O₄
• 分子量: 630.783
• InChiKey: MKZRPZIPZVNWCK-MVJOSCLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  48
• 可旋转键数：
  12
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5:3,4-dianhydro-1,6-di-O-trityl-D-altritol 在 4-二甲氨基吡啶 、 2,4,6-三异丙基苯磺酰氯 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 62.5h， 生成 4-Amino-1-((2S,3S,5S)-2,5-bis-trityloxymethyl-tetrahydro-furan-3-yl)-1H-pyrimidin-2-one
  参考文献：
  名称：

  Ring-expanded analogues of natural oxetanocin

  摘要：

  Synthesis of ring-expanded analogs of the natural compound, oxetanocin is described. The starting material for the synthesis of the series, 4-7, was D-glucosamine and introduction of the base moiety was done through the stereochemically appropriate epoxide. For the enantiomeric series, 8-11, the starting material was D-glucose and preparation of the key intermediate involved a rearrangement reaction. The structures of the target molecules were established by NMR, HRMS, optical rotation and UV data. Single-crystal X-ray data confirmed the enantiomeric structural assignments. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.087
• 作为产物：
  描述：

  2,5-脱水-d-甘露糖 在 吡啶 、 sodium tetrahydroborate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 生成 2,5:3,4-dianhydro-1,6-di-O-trityl-D-altritol
  参考文献：
  名称：

  Synthesis of 3-deoxy-3-nucleobase-2,5-anhydro-d-mannitol: a novel class of hydroxymethyl-branched isonucleosides

  摘要：

  A concise synthesis of 3-deoxy-3-nucleobase-2,5-anhydro-D-mannitol 6(a-d) has been achieved, using the deamination of 2-amino-2-deoxy-D-glucose to construct in one step the sugar skeleton with the desired sense of chirality at each asymmetric center. The selective dibenzoylation of 2,5-anhydro-D-mannitol 9 was investigated, and the key epoxide intermediate 13 was obtained in good yield via an intramolecular Mitsunobu reaction. The process of opening of epoxide 13 by nucleobases appeared to be regioselective. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00246-9

文献信息

• Efficient and Easy Access to Optically Pure Tetrasubstituted Tetra­hydrofurans via Stereoselective Opening of<i>C</i>₂-Symmetric Epoxide and Aziridine Rings
  作者：Venkata Pavan Kumar Kondapi、Olivier-Mohamad Soueidan、Seyedeh Nargess Hosseini、Nauras Jabari、Frederick G. West

  DOI：10.1002/ejoc.201501540

  日期：2016.3

  An efficient and facile protocol to functionalize position C-3 of 2,5-anhydro-D-mannitol via diastereoselective ring opening of a C2-symmetric epoxide 2,5:3,4-dianhydro-D-allitol 3 has been developed. This method is protecting-group-free, high-yielding, and provides access to C-3-modified 2,5-anhydro-D-mannitols 5a, 11a–15a and 16–17. This method was then extrapolated to the synthesis of a C2-symmetric

  已开发出一种有效且简便的方案，通过 C2 对称环氧化物 2,5:3,4-二脱水-D-甘露醇 3 的非对映选择性开环功能化 2,5-脱水-D-甘露醇的 C-3 位。该方法无保护基团，产量高，可提供 C-3 修饰的 2,5-脱水-D-甘露醇 5a、11a-15a 和 16-17。然后将此方法外推到 C2 对称氮丙啶的合成，该方法与各种亲核试剂进行开环，以优异的方式获得 C-3-和 C-4-修饰的 2,5-脱水-D-甘露醇 19-27全球产量和中等至良好的非对映选择性。这些结构及其衍生物可用于多种应用，包括如二胺单磺酰胺 28a 和 28b 所证明的不对称迈克尔加成的有机催化，
• Synthesis of 3-deoxy-3-nucleobase-2,5-anhydro-d-mannitol: a novel class of hydroxymethyl-branched isonucleosides
  作者：Z Lei、J.M Min、L.H Zhang

  DOI：10.1016/s0957-4166(00)00246-9

  日期：2000.7

  A concise synthesis of 3-deoxy-3-nucleobase-2,5-anhydro-D-mannitol 6(a-d) has been achieved, using the deamination of 2-amino-2-deoxy-D-glucose to construct in one step the sugar skeleton with the desired sense of chirality at each asymmetric center. The selective dibenzoylation of 2,5-anhydro-D-mannitol 9 was investigated, and the key epoxide intermediate 13 was obtained in good yield via an intramolecular Mitsunobu reaction. The process of opening of epoxide 13 by nucleobases appeared to be regioselective. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Ring-expanded analogues of natural oxetanocin
  作者：Vasu Nair、Byoung-Kwon Chun、Jean John Vadakkan

  DOI：10.1016/j.tet.2004.08.087

  日期：2004.11

  Synthesis of ring-expanded analogs of the natural compound, oxetanocin is described. The starting material for the synthesis of the series, 4-7, was D-glucosamine and introduction of the base moiety was done through the stereochemically appropriate epoxide. For the enantiomeric series, 8-11, the starting material was D-glucose and preparation of the key intermediate involved a rearrangement reaction. The structures of the target molecules were established by NMR, HRMS, optical rotation and UV data. Single-crystal X-ray data confirmed the enantiomeric structural assignments. (C) 2004 Elsevier Ltd. All rights reserved.