[(2R,3R,4R)-3-formyloxy-4-methyl-2-(4-methylbenzoyl)oxy-5-oxo-4-phenylmethoxypentyl] 4-methylbenzoate | 801316-48-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2R,3R,4R)-3-formyloxy-4-methyl-2-(4-methylbenzoyl)oxy-5-oxo-4-phenylmethoxypentyl] 4-methylbenzoate
• CAS: 801316-48-3
• 化学式: C₃₀H₃₀O₈
• 分子量: 518.563
• InChiKey: XFNQGNJJCCPRBY-ZKKGZRQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R)-3-formyloxy-4-methyl-2-(4-methylbenzoyl)oxy-5-oxo-4-phenylmethoxypentyl] 4-methylbenzoate 在 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 、 [(3R,4R,5R)-6-hydroxy-5-methyl-4-(4-methylbenzoyl)oxy-5-phenylmethoxyoxan-3-yl] 4-methylbenzoate
  参考文献：
  名称：

  Preparation of C-3,5-Acyl Furanoses via Highly Selective Intramolecular Acyl Migration

  摘要：

  A practical synthesis of C-3,5-acyl furanose via a base-catalyzed, highly selective intramolecular acyl migration in alcohol solvents is reported.

  DOI：

  10.1021/jo049121y
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 sodium hypochlorite 、 sodium acetate 吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 氢氧化钾 、 sodium hypochlorite 、 tetrafluoroboric acid 、 硫酸 、 20-[4-(1,1,3,3-四甲基丁基)苯氧基]-3,6,9,12,15,18-六氧杂二十烷-1-醇 、 过碘酸 、 sodium bromide 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， 反应 36.33h， 生成 [(2R,3R,4R)-3-formyloxy-4-methyl-2-(4-methylbenzoyl)oxy-5-oxo-4-phenylmethoxypentyl] 4-methylbenzoate
  参考文献：
  名称：

  Practical Synthesis of a Potent Hepatitis C Virus RNA Replication Inhibitor

  摘要：

  A practical, efficient synthesis of 1, a hepatitis C virus RNA replication inhibitor, is described. Starting with the inexpensive diacetone glucose, the 12-step synthesis features a novel stereoselective rearrangement to prepare the key crystalline furanose diol intermediate. This is followed by a highly selective glycosidation to couple the C-2 branched furanose epoxide with deazapurine.

  DOI：

  10.1021/jo0491096

文献信息

• Practical Synthesis of a Potent Hepatitis C Virus RNA Replication Inhibitor
  作者：Matthew M. Bio、Feng Xu、Marjorie Waters、J. Michael Williams、Kimberly A. Savary、Cameron J. Cowden、Chunhua Yang、Elizabeth Buck、Zhiguo J. Song、David M. Tschaen、R. P. Volante、Robert A. Reamer、Edward J. J. Grabowski

  DOI：10.1021/jo0491096

  日期：2004.9.1

  A practical, efficient synthesis of 1, a hepatitis C virus RNA replication inhibitor, is described. Starting with the inexpensive diacetone glucose, the 12-step synthesis features a novel stereoselective rearrangement to prepare the key crystalline furanose diol intermediate. This is followed by a highly selective glycosidation to couple the C-2 branched furanose epoxide with deazapurine.
• Preparation of C-3,5-Acyl Furanoses via Highly Selective Intramolecular Acyl Migration
  作者：Feng Xu、Bryon Simmons、Kimberly Savary、Chunhua Yang、Robert A. Reamer

  DOI：10.1021/jo049121y

  日期：2004.10.1

  A practical synthesis of C-3,5-acyl furanose via a base-catalyzed, highly selective intramolecular acyl migration in alcohol solvents is reported.