(2R,3R,4R,5R)-2-[(E)-2-[(2R,3R,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]ethenyl]-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane | 899435-82-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5R)-2-[(E)-2-[(2R,3R,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]ethenyl]-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane
• CAS: 899435-82-6
• 化学式: C₅₄H₅₆O₈
• 分子量: 833.034
• InChiKey: IOYZTVLSKADLNT-WWNIOUAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  62
• 可旋转键数：
  22
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-2-[(E)-2-[(2R,3R,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]ethenyl]-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane 在 Wilkinson's catalyst 吡啶 、 硫酸 、 氢气 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 41.5h， 生成 (2R,3R,4R,5R)-2-[2-[(2R,3R,4R,5R)-3,4-bis(phenylmethoxy)-5-(trityloxymethyl)oxolan-2-yl]ethyl]-5-(octoxymethyl)-3,4-bis(phenylmethoxy)oxolane
  参考文献：
  名称：

  An olefin cross metathesis approach to C-disaccharide analogs of the α-d-arabinofuranosyl-(1→5)-α-d-arabinofuranoside motif found in the mycobacterial cell wall

  摘要：

  Reported is the synthesis of a C-disaccharide analog of the alpha-D-Araf-(1 -> 5)-alpha-D-Araf motif present in the cell wall of mycobacteria, including the human pathogen Mycobacterium tuberculosis. The key step is an olefin cross metathesis reaction that proceeds in excellent yield and which can be carried out on mmol scale. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.008
• 作为产物：
  描述：

  (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-((E)-propenyl)-tetrahydro-furan 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以96%的产率得到(2R,3R,4R,5R)-2-[(E)-2-[(2R,3R,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]ethenyl]-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane
  参考文献：
  名称：

  An olefin cross metathesis approach to C-disaccharide analogs of the α-d-arabinofuranosyl-(1→5)-α-d-arabinofuranoside motif found in the mycobacterial cell wall

  摘要：

  Reported is the synthesis of a C-disaccharide analog of the alpha-D-Araf-(1 -> 5)-alpha-D-Araf motif present in the cell wall of mycobacteria, including the human pathogen Mycobacterium tuberculosis. The key step is an olefin cross metathesis reaction that proceeds in excellent yield and which can be carried out on mmol scale. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.008

文献信息

• An olefin cross metathesis approach to C-disaccharide analogs of the α-d-arabinofuranosyl-(1→5)-α-d-arabinofuranoside motif found in the mycobacterial cell wall
  作者：Grace X. Chang、Todd L. Lowary

  DOI：10.1016/j.tetlet.2006.05.008

  日期：2006.7

  Reported is the synthesis of a C-disaccharide analog of the alpha-D-Araf-(1 -> 5)-alpha-D-Araf motif present in the cell wall of mycobacteria, including the human pathogen Mycobacterium tuberculosis. The key step is an olefin cross metathesis reaction that proceeds in excellent yield and which can be carried out on mmol scale. (c) 2006 Elsevier Ltd. All rights reserved.