(-)-(2R,3R,4S)-4-benzyloxy-6-methoxy-3-methyl-tetrahydropyran-2-acetic acid methyl ester | 243849-45-8

• 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,4S)-4-benzyloxy-6-methoxy-3-methyl-tetrahydropyran-2-acetic acid methyl ester
• 英文别名: methyl 2-[(2R,3R,4S)-6-methoxy-3-methyl-4-phenylmethoxyoxan-2-yl]acetate
• CAS: 243849-45-8
• 化学式: C₁₇H₂₄O₅
• 分子量: 308.375
• InChiKey: DEUMTXKBXHOXRR-NHCAMLGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-(2R,3R,4S)-4-benzyloxy-6-methoxy-3-methyl-tetrahydropyran-2-acetic acid methyl ester 在 咪唑 、 四丁基碘化铵 、 二异丁基氢化铝 、 碳酸氢钠 、 间氯过氧苯甲酸 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.42h， 生成 (2R,3R,4S,6R)-6-benzenesulfonyl-4-benzyloxy-2-(2-triethylsilyloxy-ethyl)-3-methyl-tetrahydropyran
  参考文献：
  名称：

  Synthesis of the C29–C37 segment of spongistatin 1

  摘要：

  Starting from racemic 2 alpha-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one the spongistatin E segment has been prepared in nine steps (2.3 steps per stereogenic center) with umpolung of anomeric reactivity at C37. This 3,5-syn-diol sequence completes our methodology to all stereoisomers of 3,5,7-trihydroxy heptanoic ester building blocks functionalized for alpha-oxyanion chemistry. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00148-2
• 作为产物：
  描述：

  (-)-(1S,5R,6R,7S)-7-benzyloxy-6-methyl-2,9-dioxabicycli<3.3.1>nonan-3-one 、 原甲酸三甲酯 在 硫酸 作用下， 以 甲醇 为溶剂， 以99%的产率得到(-)-(2R,3R,4S)-4-benzyloxy-6-methoxy-3-methyl-tetrahydropyran-2-acetic acid methyl ester
  参考文献：
  名称：

  Synthesis of the C29–C37 segment of spongistatin 1

  摘要：

  Starting from racemic 2 alpha-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one the spongistatin E segment has been prepared in nine steps (2.3 steps per stereogenic center) with umpolung of anomeric reactivity at C37. This 3,5-syn-diol sequence completes our methodology to all stereoisomers of 3,5,7-trihydroxy heptanoic ester building blocks functionalized for alpha-oxyanion chemistry. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00148-2

文献信息

• Synthesis of the C29–C37 segment of spongistatin 1
  作者：Ralf Dunkel、Jens Treu、H.Martin R Hoffmann

  DOI：10.1016/s0957-4166(99)00148-2

  日期：1999.4

  Starting from racemic 2 alpha-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one the spongistatin E segment has been prepared in nine steps (2.3 steps per stereogenic center) with umpolung of anomeric reactivity at C37. This 3,5-syn-diol sequence completes our methodology to all stereoisomers of 3,5,7-trihydroxy heptanoic ester building blocks functionalized for alpha-oxyanion chemistry. (C) 1999 Elsevier Science Ltd. All rights reserved.