(2R,4R,5S,6R)-2,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid isopropyl ester | 188955-38-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4R,5S,6R)-2,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid isopropyl ester
• 英文别名: propan-2-yl (2R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxane-2-carboxylate
• CAS: 188955-38-6
• 化学式: C₁₀H₁₈O₇
• 分子量: 250.249
• InChiKey: BAFZFYSQWGFQPA-BDNRQGISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,4R,5S,6R)-2,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid isopropyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以83%的产率得到3-deoxy-D-arabino-2-heptulopyranosonic acid
  参考文献：
  名称：

  Indium mediated allylation in carbohydrate chemistry: A convenient synthesis of 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and 3-deoxy-D-arabino-2-heptulose (kamusol)

  摘要：

  A short and economical synthesis of 3-deoxy-D-arabino-2-heptulosonic acid (4) and 3-deoxy-D-arabino-2-heptulose (kamusol, 8) has been developed. In the key step of the reaction sequence, the indium mediated allylation of D-erythrose in an aqueous solvent system was utilized generating a seven carbon backbone which was further transformed into the title compounds.

  DOI：

  10.1007/bf00807577
• 作为产物：
  描述：

  (5S,6R)-4,5,6,7-Tetrahydroxy-2-methylene-heptanoic acid isopropyl ester 在 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以48%的产率得到(2R,4R,5S,6R)-2,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid isopropyl ester
  参考文献：
  名称：

  Indium mediated allylation in carbohydrate chemistry: A convenient synthesis of 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and 3-deoxy-D-arabino-2-heptulose (kamusol)

  摘要：

  A short and economical synthesis of 3-deoxy-D-arabino-2-heptulosonic acid (4) and 3-deoxy-D-arabino-2-heptulose (kamusol, 8) has been developed. In the key step of the reaction sequence, the indium mediated allylation of D-erythrose in an aqueous solvent system was utilized generating a seven carbon backbone which was further transformed into the title compounds.

  DOI：

  10.1007/bf00807577

文献信息

• Indium mediated allylation in carbohydrate chemistry: A convenient synthesis of 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and 3-deoxy-D-arabino-2-heptulose (kamusol)
  作者：R. H. Prenner、W. Schmid

  DOI：10.1007/bf00807577

  日期：1996.10

  A short and economical synthesis of 3-deoxy-D-arabino-2-heptulosonic acid (4) and 3-deoxy-D-arabino-2-heptulose (kamusol, 8) has been developed. In the key step of the reaction sequence, the indium mediated allylation of D-erythrose in an aqueous solvent system was utilized generating a seven carbon backbone which was further transformed into the title compounds.