(2R,3R,4R,5S,6S)-3,4,5-tris(methoxymethoxy)-2-(methoxymethoxymethyl)-6-[(4-nitrophenyl)methyl]oxane | 478068-25-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5S,6S)-3,4,5-tris(methoxymethoxy)-2-(methoxymethoxymethyl)-6-[(4-nitrophenyl)methyl]oxane
• CAS: 478068-25-6
• 化学式: C₂₁H₃₃NO₁₁
• 分子量: 475.493
• InChiKey: JJYHSUKHASUZRH-QGLKVJOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S,6S)-3,4,5-tris(methoxymethoxy)-2-(methoxymethoxymethyl)-6-[(4-nitrophenyl)methyl]oxane 在 sodium hydroxide 、 palladium on activated charcoal 、 potassium bromide 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 氯化亚砜 、 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 20.0~40.0 ℃ 、275.79 kPa 条件下， 反应 51.0h， 生成 (Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4-retinamidophenylmethane
  参考文献：
  名称：

  An improved synthesis of the C-linked glucuronide of N-(4-Hydroxyphenyl)retinamide

  摘要：

  Retinoic acid analogues such as N-(4-hydroxyphenyl)retinamide (4-HPR) are effective chemopreventatives and chemotherapeutics for numerous types of cancer. The C-linked analogue of the O-glucuronide of 4-HPR (4-HPRCG) has been shown to be a more effective agent. The synthetic route to this molecule has been significantly improved by access to a key C-benzyl-glucuronide intermediate through employment of a Suzuki coupling reaction between an exoanomeric methylene sugar and an aryl bromide. Preliminary evidence shows 4-HPRCG has chemotherapeutic activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00427-4
• 作为产物：
  描述：

  葡萄糖酸内酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 、 四丁基碘化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 90.0h， 生成 (2R,3R,4R,5S,6S)-3,4,5-tris(methoxymethoxy)-2-(methoxymethoxymethyl)-6-[(4-nitrophenyl)methyl]oxane
  参考文献：
  名称：

  An improved synthesis of the C-linked glucuronide of N-(4-Hydroxyphenyl)retinamide

  摘要：

  Retinoic acid analogues such as N-(4-hydroxyphenyl)retinamide (4-HPR) are effective chemopreventatives and chemotherapeutics for numerous types of cancer. The C-linked analogue of the O-glucuronide of 4-HPR (4-HPRCG) has been shown to be a more effective agent. The synthetic route to this molecule has been significantly improved by access to a key C-benzyl-glucuronide intermediate through employment of a Suzuki coupling reaction between an exoanomeric methylene sugar and an aryl bromide. Preliminary evidence shows 4-HPRCG has chemotherapeutic activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00427-4

文献信息

• An improved synthesis of the C-linked glucuronide of N-(4-Hydroxyphenyl)retinamide
  作者：Joel R. Walker、Galal Alshafie、Hussein Abou-Issa、Robert W. Curley

  DOI：10.1016/s0960-894x(02)00427-4

  日期：2002.9

  Retinoic acid analogues such as N-(4-hydroxyphenyl)retinamide (4-HPR) are effective chemopreventatives and chemotherapeutics for numerous types of cancer. The C-linked analogue of the O-glucuronide of 4-HPR (4-HPRCG) has been shown to be a more effective agent. The synthetic route to this molecule has been significantly improved by access to a key C-benzyl-glucuronide intermediate through employment of a Suzuki coupling reaction between an exoanomeric methylene sugar and an aryl bromide. Preliminary evidence shows 4-HPRCG has chemotherapeutic activity. (C) 2002 Elsevier Science Ltd. All rights reserved.