[(4S,5R)-5-hydroxy-4,6-bis(phenylmethoxy)hexyl] 2,2-dimethylpropanoate | 223575-44-8

• 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: [(4S,5R)-5-hydroxy-4,6-bis(phenylmethoxy)hexyl] 2,2-dimethylpropanoate
• CAS: 223575-44-8
• 化学式: C₂₅H₃₄O₅
• 分子量: 414.542
• InChiKey: CLLOWJABOZKKJO-PKTZIBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(4S,5R)-5-hydroxy-4,6-bis(phenylmethoxy)hexyl] 2,2-dimethylpropanoate 在 盐酸 、 草酰氯 、 甲基锂 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 66.0h， 生成 (6S,7R,E)-7-hydroxy-3-methyl-6,8-diphenylmethoxy-2-octanoic acid ethyl ester
  参考文献：
  名称：

  Radical-Mediated Construction of Cyclopentane with Concurrent Formation of a Well-Defined Quaternary Center

  摘要：

  Synthetic efforts toward the total synthesis of clavulactone dealing with enantioselective construction of the cyclopentane moiety are reported. With a novel radical-mediated cyclization as key step, the current approach allows for concurrent enantioselective construction of a quaternary chiral carbon at the cyclization step. The stereochemistries of the newly formed chiral centers are dictated by the configuration of the C-1 (cf. numbering in 1). The high selectivity observed in this work is ascribed to the conformational advantage of the cyclic acetal, which results in a much better defined transition state than the previously used open-chain counterpart does.

  DOI：

  10.1021/jo9822380
• 作为产物：
  描述：

  ethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium tetrahydroborate 、 氢气 、 sodium hydride 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 47.0h， 生成 [(4S,5R)-5-hydroxy-4,6-bis(phenylmethoxy)hexyl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Radical-Mediated Construction of Cyclopentane with Concurrent Formation of a Well-Defined Quaternary Center

  摘要：

  Synthetic efforts toward the total synthesis of clavulactone dealing with enantioselective construction of the cyclopentane moiety are reported. With a novel radical-mediated cyclization as key step, the current approach allows for concurrent enantioselective construction of a quaternary chiral carbon at the cyclization step. The stereochemistries of the newly formed chiral centers are dictated by the configuration of the C-1 (cf. numbering in 1). The high selectivity observed in this work is ascribed to the conformational advantage of the cyclic acetal, which results in a much better defined transition state than the previously used open-chain counterpart does.

  DOI：

  10.1021/jo9822380

文献信息

• Radical-Mediated Construction of Cyclopentane with Concurrent Formation of a Well-Defined Quaternary Center
  作者：Qiang Zhu、Li-Xin Qiao、Yikang Wu、Yu-Lin Wu

  DOI：10.1021/jo9822380

  日期：1999.4.1

  Synthetic efforts toward the total synthesis of clavulactone dealing with enantioselective construction of the cyclopentane moiety are reported. With a novel radical-mediated cyclization as key step, the current approach allows for concurrent enantioselective construction of a quaternary chiral carbon at the cyclization step. The stereochemistries of the newly formed chiral centers are dictated by the configuration of the C-1 (cf. numbering in 1). The high selectivity observed in this work is ascribed to the conformational advantage of the cyclic acetal, which results in a much better defined transition state than the previously used open-chain counterpart does.