2-((4S,5S)-5-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol | 562823-71-6

• 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)ethanol
• 英文别名: 2-[(4S,5S)-2,2-dimethyl-5-(phenylmethoxymethyl)-1,3-dioxolan-4-yl]ethanol
• CAS: 562823-71-6
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: PHRCNQVCSYIENB-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 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)ethanol 在 咪唑 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 草酰氯 、 palladium 10% on activated carbon 、 三氟化硼乙醚 、 potassium tert-butylate 、 四丁基氟化铵 、 氢气 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 85.33h， 生成 (4S,5S,8S,10R,E)-4,5,8-trihydroxy-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one
  参考文献：
  名称：

  A facile chiral pool synthesis of 9-epi-decarestrictine-D, decarestrictine-D and O

  摘要：

  A facile chiral pool total synthesis of 9-epi-decarestrictine-D, decarestrictine-D and O has been achieved from L-(+)-diethyl tartrate. The strategy utilized is conventional and flexible. Wittig homologation and Grubbs ring closing metathesis are the key reactions employed for the synthesis of the title molecules. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.12.008
• 作为产物：
  描述：

  (4R,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester 在 锂硼氢 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 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

文献信息

• 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.
• A facile chiral pool synthesis of 9-epi-decarestrictine-D, decarestrictine-D and O
  作者：Kuchena Vamshikrishna、Garlapati Srinu、Pabbaraja Srihari

  DOI：10.1016/j.tetasy.2013.12.008

  日期：2014.2

  A facile chiral pool total synthesis of 9-epi-decarestrictine-D, decarestrictine-D and O has been achieved from L-(+)-diethyl tartrate. The strategy utilized is conventional and flexible. Wittig homologation and Grubbs ring closing metathesis are the key reactions employed for the synthesis of the title molecules. (C) 2013 Elsevier Ltd. All rights reserved.
• 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。