(2S,3S,4R,5R)-2-methoxy-5-(nitromethyl)-3,4-bis(phenylmethoxy)oxolane | 492470-85-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5R)-2-methoxy-5-(nitromethyl)-3,4-bis(phenylmethoxy)oxolane
• CAS: 492470-85-6
• 化学式: C₂₀H₂₃NO₆
• 分子量: 373.406
• InChiKey: IWEYVRPZPDZIPD-ZRNYENFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R)-2-methoxy-5-(nitromethyl)-3,4-bis(phenylmethoxy)oxolane 在 吡啶 、 potassium fluoride 、 18-冠醚-6 、 乙酸酐 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 15.5h， 生成
  参考文献：
  名称：

  First synthesis of methyl α-C-d-arabinofuranosyl-(1→5)-α-d-arabinofuranoside: the C-disaccharide segment of motif C of Mycobacterium tuberculosis

  摘要：

  The synthesis of C-analogue of the disaccharide 2 alpha-araf-(1-->5)-ara present in motif C of the arabino-galactan portion of Mycobacterium tuberculosis, has been described. The critical C-C bond formation reaction to couple both the furanosyl residues has been accomplished through nitro-aldol condensation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01760-4
• 作为产物：
  描述：

  methyl 2,3-di-O-benzyl-α-D-arabinofuranoside 在 咪唑 、 间苯三酚 、 碘 、 三苯基膦 、 sodium nitrite 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 73.5h， 生成 (2S,3S,4R,5R)-2-methoxy-5-(nitromethyl)-3,4-bis(phenylmethoxy)oxolane
  参考文献：
  名称：

  First synthesis of methyl α-C-d-arabinofuranosyl-(1→5)-α-d-arabinofuranoside: the C-disaccharide segment of motif C of Mycobacterium tuberculosis

  摘要：

  The synthesis of C-analogue of the disaccharide 2 alpha-araf-(1-->5)-ara present in motif C of the arabino-galactan portion of Mycobacterium tuberculosis, has been described. The critical C-C bond formation reaction to couple both the furanosyl residues has been accomplished through nitro-aldol condensation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01760-4

文献信息

• First synthesis of methyl α-C-d-arabinofuranosyl-(1→5)-α-d-arabinofuranoside: the C-disaccharide segment of motif C of Mycobacterium tuberculosis
  作者：Mukund K. Gurjar、Ravi Nagaprasad、C.V. Ramana

  DOI：10.1016/s0040-4039(02)01760-4

  日期：2002.10

  The synthesis of C-analogue of the disaccharide 2 alpha-araf-(1-->5)-ara present in motif C of the arabino-galactan portion of Mycobacterium tuberculosis, has been described. The critical C-C bond formation reaction to couple both the furanosyl residues has been accomplished through nitro-aldol condensation. (C) 2002 Elsevier Science Ltd. All rights reserved.