[2-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-diphenyl-silane | 562823-57-8

• 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: [2-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-diphenyl-silane
• 英文别名: tert-butyl-[2-[(4S,5S)-2,2-dimethyl-5-(phenylmethoxymethyl)-1,3-dioxolan-4-yl]ethoxy]-diphenylsilane
• CAS: 562823-57-8
• 化学式: C₃₁H₄₀O₄Si
• 分子量: 504.742
• InChiKey: BQCGHFZXGOTJDY-VMPREFPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.69
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-diphenyl-silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以99%的产率得到2-((4S,5S)-5-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol
  参考文献：
  名称：

  抗肿瘤大环内酯Peloruside A C1C9 片段的对映选择性合成

  摘要：

  描述了海洋天然产物peloruside A C 1 C 9片段的立体控制合成。关键步骤包括 Sharpless 的催化不对称二羟基化反应、手性 β-烷氧基酮的螯合控制还原以形成顺式-1,3-二醇官能团以及高烯丙醇衍生的丙烯酸酯的闭环烯烃复分解反应以形成α,β-不饱和δ-内酯。

  DOI：

  10.1016/s0040-4039(03)00744-5
• 作为产物：
  描述：

  3-(tert-butyldiphenylsilyloxy)-1-propanal 在 AD-mix-α 、 正丁基锂 、 甲基磺酰胺 、 水 、 sodium hydride 、 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 环己烷 、 叔丁醇 、 苯 为溶剂， 反应 1.67h， 生成 [2-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-diphenyl-silane
  参考文献：
  名称：

  Enantioselective Synthesis and Biological Activity of (3S,4R)- and (3S,4S)-3-Hydroxy-4-hydroxymethyl- 4-butanolides in Relation to PGE₂

  摘要：

  Compounds 9 and 13 were synthesized, and their structures and stereochemistry were elucidated by spectroscopic methods. In competition binding experiments, specific [H-3]-PGE(2) binding was significantly displaced by compound 9 and, to a lesser extent, by 13, in a dose-dependent manner. The biological properties of compound 9 were studied on HL-60 cells, and several effects were found related to those of PGE(2). Compound 9 increases c-fos mRNA level as does PGE2 and antagonizes TPA-induced terminal differentiation.

  DOI：

  10.1021/jm034216y

文献信息

• An enantioselective synthesis of the C1C9 segment of antitumor macrolide peloruside A
  作者：Arun K. Ghosh、Jae-Hun Kim

  DOI：10.1016/s0040-4039(03)00744-5

  日期：2003.5

  A stereocontrolled synthesis of the C1C9 segment of the marine natural product peloruside A is described. The key steps involve Sharpless's catalytic asymmetric dihydroxylation reaction, a chelation-controlled reduction of chiral β-alkoxy ketones to elaborate the syn-1,3-diol functionality and a ring-closing olefin metathesis of a homoallylic alcohol-derived acrylate ester to form an α,β-unsaturated

  描述了海洋天然产物peloruside A C 1 C 9片段的立体控制合成。关键步骤包括 Sharpless 的催化不对称二羟基化反应、手性 β-烷氧基酮的螯合控制还原以形成顺式-1,3-二醇官能团以及高烯丙醇衍生的丙烯酸酯的闭环烯烃复分解反应以形成α,β-不饱和δ-内酯。
• Enantioselective Synthesis and Biological Activity of (3<i>S</i>,4<i>R</i>)- and (3<i>S</i>,4<i>S</i>)-3-Hydroxy-4-hydroxymethyl- 4-butanolides in Relation to PGE₂
  作者：Pedro O. Miranda、Francisco Estévez、José Quintana、Candelaria I. García、Ignacio Brouard、Juan I. Padrón、Juan P. Pivel、Jaime Bermejo

  DOI：10.1021/jm034216y

  日期：2004.1.1

  Compounds 9 and 13 were synthesized, and their structures and stereochemistry were elucidated by spectroscopic methods. In competition binding experiments, specific [H-3]-PGE(2) binding was significantly displaced by compound 9 and, to a lesser extent, by 13, in a dose-dependent manner. The biological properties of compound 9 were studied on HL-60 cells, and several effects were found related to those of PGE(2). Compound 9 increases c-fos mRNA level as does PGE2 and antagonizes TPA-induced terminal differentiation.