[(1R,2R,3R)-2-benzoyloxy-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxybutyl] benzoate | 189702-35-0

• 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: [(1R,2R,3R)-2-benzoyloxy-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxybutyl] benzoate
• CAS: 189702-35-0
• 化学式: C₂₃H₂₆O₈
• 分子量: 430.455
• InChiKey: RXQDPTKFIPOXCZ-UAFMIMERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(1R,2R,3R)-2-benzoyloxy-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxybutyl] benzoate 在 4-二甲氨基吡啶 、 氢氧化钾 、 N,N-二异丙基乙胺 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 44.5h， 生成 [(1S,2R,3R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxy-3,4-bis(phenylmethoxymethoxy)butyl] benzoate
  参考文献：
  名称：

  Diastereoselective Grignard Additions to O-Protected Polyhydroxylated Ketones:  A Reaction Controlled by Groundstate Conformation?

  摘要：

  The O-protected polyhydroxy ketones 9-14 and 39, 42 add sigma-type Grignard reagents with >90:10 stereoselectivity to give the 3,4-syn-adducts 17-28 and 43, 45, respectively, as the major diastereomers (Tables 1 and 2). The stereoselectivity is interpreted in terms of early transition states which are very close to the groundstate conformations shown in Figure 6 and 7. These demonstrate that the ''top face'' of the carbonyl group is much less shielded than the ''bottom'' face. Complexation phenomena are of minor importance. It is also shown that the classical transition state models (Felkin-Anh or chelate Cram) are not applicable to polyoxygenated ketones.

  DOI：

  10.1021/jo961542v
• 作为产物：
  描述：

  双丙酮-D-甘露糖醇 在 4-二甲氨基吡啶 、 三乙胺 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 [(1R,2R,3R)-2-benzoyloxy-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxybutyl] benzoate
  参考文献：
  名称：

  Eldecalcitol 的高度立体选择性和可规模化合成

  摘要：

  发表于《国际有机制备和程序：有机合成新期刊》（第 56 卷，第 1 期，2024 年）

  DOI：

  10.1080/00304948.2023.2219200

文献信息

• Diastereoselective Grignard Additions to <i>O</i>-Protected Polyhydroxylated Ketones:  A Reaction Controlled by Groundstate Conformation?
  作者：Johann Mulzer、Catarina Pietschmann、Jürgen Buschmann、Peter Luger

  DOI：10.1021/jo961542v

  日期：1997.6.13

  The O-protected polyhydroxy ketones 9-14 and 39, 42 add sigma-type Grignard reagents with >90:10 stereoselectivity to give the 3,4-syn-adducts 17-28 and 43, 45, respectively, as the major diastereomers (Tables 1 and 2). The stereoselectivity is interpreted in terms of early transition states which are very close to the groundstate conformations shown in Figure 6 and 7. These demonstrate that the ''top face'' of the carbonyl group is much less shielded than the ''bottom'' face. Complexation phenomena are of minor importance. It is also shown that the classical transition state models (Felkin-Anh or chelate Cram) are not applicable to polyoxygenated ketones.
• Highly Stereoselective and Scalable Synthesis of Eldecalcitol
  作者：Xue-yan Zhu、Ya-jun Guo、Yu-hui Shen、De-yong Ye、Wei-cheng Zhou

  DOI：10.1080/00304948.2023.2219200

  日期：2024.1.2

  Published in Organic Preparations and Procedures International: The New Journal for Organic Synthesis (Vol. 56, No. 1, 2024)

  发表于《国际有机制备和程序：有机合成新期刊》（第 56 卷，第 1 期，2024 年）