(Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4-aminophenylmethane | 158419-84-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4-aminophenylmethane
• 英文别名: methyl (2S,3S,4R,5S,6S)-3,4,5-triacetyloxy-6-[(4-aminophenyl)methyl]oxane-2-carboxylate
• CAS: 158419-84-2
• 化学式: C₂₀H₂₅NO₉
• 分子量: 423.42
• InChiKey: MEWUWHLTUAPXSU-OYSTVDSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4-aminophenylmethane 在 吡啶 、 氢氧化钾 、 氯化亚砜 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 40.0h， 生成 1-(β-D-Glucopyranosyluronic acid)-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 sodium hydroxide 、 palladium on activated charcoal 、 potassium bromide 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 potassium phosphate 、 氢气 、 四丁基碘化铵 、 碳酸氢钠 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 20.0~70.0 ℃ 、275.79 kPa 条件下， 反应 137.0h， 生成 (Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4-aminophenylmethane
  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

• Panigot, M. J.; Humphries, K. A.; Curley, R. W., Journal of Carbohydrate Chemistry, 1994, vol. 13, # 2, p. 303 - 322
  作者：Panigot, M. J.、Humphries, K. A.、Curley, R. W.

  DOI：——

  日期：——
• RECENT IMPROVEMENTS TOWARDS THE SYNTHESIS OF THE C-GLUCURONOSYL CANCER CHEMOPREVENTIVE (β-d-GLUCOPYRANOSYLURONATE)-4-RETINAMIDOPHENYLMETHANE
  作者：M. F. Wong、K. L. Weiss、R. W. Curley

  DOI：10.1080/07328309608005690

  日期：1996.8