[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(S)-cyano(phenyl)methoxy]oxan-2-yl]methoxy]oxan-2-yl]methyl acetate | 61091-11-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(S)-cyano(phenyl)methoxy]oxan-2-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 61091-11-0
• 化学式: C₃₄H₄₁NO₁₈
• 分子量: 751.695
• InChiKey: VOZGJFHALJQFKA-YBBFCSJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  53
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  245
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(S)-cyano(phenyl)methoxy]oxan-2-yl]methoxy]oxan-2-yl]methyl acetate 在 palladium dihydroxide 、 三氟化硼乙醚 、 sodium hydride 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 为溶剂， -50.0~25.0 ℃ 、100.0 kPa 条件下， 反应 3.25h， 生成 (R)-phenyl-[O²,O³,O⁴-triacetyl-O⁶-(tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranosyloxy]-acetic acid
  参考文献：
  名称：

  Synthesis and evaluation of diverse analogs of amygdalin as potential peptidomimetics of peptide T

  摘要：

  Peptide T (ASTTTNYT) is a promising molecule to prevent the neuro psychometric symptoms of patients suffering AIDS and for the treatment of psoriasis. In order to fully prove its therapeutic benefits, efforts were put forward to design peptidomimetics of the peptide. In this direction, in a recent computational study the natural product amygdalin was identified as a prospective peptidomimetic of the peptide and later proved to exhibit a similar chemotactic profile to the peptide. However, the cyanide moiety of amygdalin provides to the molecule a toxic profile. The present study reports the synthesis of a set of amygdalin analogs lacking the cyanide group with improved chemotactic profiles. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.071
• 作为产物：
  描述：

  乙酸酐 、 neoamygdalin 在 吡啶 作用下， 反应 12.0h， 生成 [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(S)-cyano(phenyl)methoxy]oxan-2-yl]methoxy]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Synthesis and evaluation of diverse analogs of amygdalin as potential peptidomimetics of peptide T

  摘要：

  Peptide T (ASTTTNYT) is a promising molecule to prevent the neuro psychometric symptoms of patients suffering AIDS and for the treatment of psoriasis. In order to fully prove its therapeutic benefits, efforts were put forward to design peptidomimetics of the peptide. In this direction, in a recent computational study the natural product amygdalin was identified as a prospective peptidomimetic of the peptide and later proved to exhibit a similar chemotactic profile to the peptide. However, the cyanide moiety of amygdalin provides to the molecule a toxic profile. The present study reports the synthesis of a set of amygdalin analogs lacking the cyanide group with improved chemotactic profiles. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.071