Benzoic acid (2R,3R,5S)-5-((2R,3R,4R)-3-benzyloxy-2-methoxy-4-methyl-tetrahydro-pyran-2-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester | 862670-59-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzoic acid (2R,3R,5S)-5-((2R,3R,4R)-3-benzyloxy-2-methoxy-4-methyl-tetrahydro-pyran-2-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester
• CAS: 862670-59-5
• 化学式: C₄₂H₅₀O₇Si
• 分子量: 694.94
• InChiKey: FOSQDTVVLODTIY-PDZFXYDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.93
• 重原子数：
  50.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2R,3R,5S)-5-((2R,3R,4R)-3-benzyloxy-2-methoxy-4-methyl-tetrahydro-pyran-2-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.5h， 以86%的产率得到Benzoic acid (2R,3R,5S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-((2S,3R,4R)-3-hydroxy-2-methoxy-4-methyl-tetrahydro-pyran-2-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Synthesis of the common left-half part of pectenotoxins

  摘要：

  The common left-half [C31-C33(OCl-C7)-C40] part of pectenotoxins has been synthesized convergently from the C31-C35, C36-C40, and C1-C7 parts. The C31-C35 part, prepared via a new route shorter than our previous route, was coupled with the C36-C40 part through reductive lithiation and addition reactions to give an adduct stereoselectively, which was converted to a cyclic acetal corresponding to the C31-C40 part. The left-half was synthesized by a three-step process including esterification of the C31-C40 part with the C1-C7 part. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.062
• 作为产物：
  描述：

  (2R,3R)-5-p-methoxybenzyloxy-3-methylpentane-1,2-diol 在 吡啶 、 4-二甲氨基吡啶 、 草酰氯 、 dimethyl pimelimidate dihydrochloride 、 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium 、 camphor-10-sulfonic acid 、 二异丁基氢化铝 、 碳酸氢钠 、 二甲基亚砜 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 28.17h， 生成 Benzoic acid (2R,3R,5S)-5-((2R,3R,4R)-3-benzyloxy-2-methoxy-4-methyl-tetrahydro-pyran-2-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Synthesis of the common left-half part of pectenotoxins

  摘要：

  The common left-half [C31-C33(OCl-C7)-C40] part of pectenotoxins has been synthesized convergently from the C31-C35, C36-C40, and C1-C7 parts. The C31-C35 part, prepared via a new route shorter than our previous route, was coupled with the C36-C40 part through reductive lithiation and addition reactions to give an adduct stereoselectively, which was converted to a cyclic acetal corresponding to the C31-C40 part. The left-half was synthesized by a three-step process including esterification of the C31-C40 part with the C1-C7 part. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.062