1-[(2R,3S,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]-2-[(2R,3R,4S,5S)-5-methoxy-3,4-bis(phenylmethoxy)oxolan-2-yl]-2-nitroethanol | 492470-84-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(2R,3S,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]-2-[(2R,3R,4S,5S)-5-methoxy-3,4-bis(phenylmethoxy)oxolan-2-yl]-2-nitroethanol
• CAS: 492470-84-5
• 化学式: C₄₇H₅₁NO₁₁
• 分子量: 805.922
• InChiKey: RCQCGGOUYMWBLS-COBLJENYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  59
• 可旋转键数：
  20
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-[(2R,3S,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]-2-[(2R,3R,4S,5S)-5-methoxy-3,4-bis(phenylmethoxy)oxolan-2-yl]-2-nitroethanol 在 吡啶 、 sodium tetrahydroborate 、 偶氮二异丁腈 、 三正丁基氢锡 、 乙酸酐 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 15.5h， 生成 methyl 2,3-di-O-benzyl-6-C-(2,3,5-tri-O-benzyl-α-D-arabinofuranosyl)-5,6-dideoxy-α-D-arabino-hexofuranoside
  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：

  2,5-anhydro-3,4-di-O-benzyl-D-mannitol 在 potassium fluoride 、 草酰氯 、 18-冠醚-6 、 sodium hydride 、 二甲基亚砜 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.5h， 生成 1-[(2R,3S,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]-2-[(2R,3R,4S,5S)-5-methoxy-3,4-bis(phenylmethoxy)oxolan-2-yl]-2-nitroethanol
  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.