methyl 3-(3,4-dimethoxy-benzyloxy)-2-(R)-methyl-propionate | 212051-39-3

• 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: methyl 3-(3,4-dimethoxy-benzyloxy)-2-(R)-methyl-propionate
• 英文别名: methyl (2R)-3-[(3,4-dimethoxyphenyl)methoxy]-2-methylpropanoate
• CAS: 212051-39-3
• 化学式: C₁₄H₂₀O₅
• 分子量: 268.31
• InChiKey: PTDXDEOSGWRJMA-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-(3,4-dimethoxy-benzyloxy)-2-(R)-methyl-propionate 在 异丙基氯化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 (R)-3-(3,4-dimethoxybenzyloxy)-2-methylbutan-3-one
  参考文献：
  名称：

  （+）-dolastatin 19的总合成和立体化学重新分配，Doastella auricularia分离出的一种细胞毒性海洋大环内酯

  摘要：

  利用构象分析和生物遗传学的考虑，提出了针对细胞毒性海洋大环内酯多拉汀19的修订构型分配，并通过完成第一个总合成对其进行了验证。高度立体控制的路线的主要特征包括不对称的乙烯基Mukaiyama羟醛反应，可同时安装远程C13立体中心和C10-C11（E）-三取代的烯烃，两个顺序的1,4-顺硼硼介导的羟醛反应，以及一个后期反应。阶段的α选择性Mukaiyama糖基化反应，以附加l-鼠李糖衍生的吡喃糖苷。

  DOI：

  10.1016/j.tet.2007.01.048
• 作为产物：
  描述：

  3,4-二甲氧基苄醇 在 草酰氯 、 4-甲基苯磺酸吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 11.75h， 生成 methyl 3-(3,4-dimethoxy-benzyloxy)-2-(R)-methyl-propionate
  参考文献：
  名称：

  Preparation and reaction of 4-methoxybenzyl (MPM) and 3,4-dimethoxybenzyl (DMPM) perfluoroimidates

  摘要：

  We have succeeded in one-pot preparation of perfluoroimidates at -78 degrees C by employing the dehydration of perfluoroamide under the "activated" dimethyl sulfoxide (DMSO) species followed by in situ nitrile trapping with alcohols. MPM and DMPM perfluoroimidates can be used to protect alcohols in place of the trichloroacetimidate with excellent chemical properties and in comparable yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01121-6

文献信息

• Stereocontrolled Total Synthesis of (−)-Callipeltoside A
  作者：Ian Paterson、Robert D. M. Davies、Annekatrin C. Heimann、Rodolfo Marquez、Arndt Meyer

  DOI：10.1021/ol0357853

  日期：2003.11.1

  text] A highly stereocontrolled total synthesis of the cytotoxic macrolide (-)-callipeltoside A has been achieved in 23 steps (4.8% overall). Notable features include a novel asymmetric vinylogous aldol reaction to install the C13 stereocenter and (E)-trisubstituted alkene, an anti-selective aldol addition, a Sonogashira coupling, and, last, a Schmidt-type glycosylation to attach the sugar unit.

  [结构：见正文]已经通过23个步骤（高度为4.8％）实现了高度立体控制的细胞毒性大环内酯（-）-卡利普利糖苷A的总合成。显着特征包括安装C13立体中心和（E）-三取代烯烃的新型不对称乙烯基醇醛醇反应，抗选择性醇醛醇加成，Sonogashira偶联以及最后的Schmidt型糖基化以连接糖单元。
• Activated dimethyl sulfoxide dehydration of amide and its application to one-pot preparation of benzyl-type perfluoroimidates
  作者：Noriyuki Nakajima、Miho Saito、Makoto Ubukata

  DOI：10.1016/s0040-4020(02)00304-6

  日期：2002.4

  Various types of primary amides were treated under an activated dimethyl sulfoxide (DMSO) species, (COCl)(2)-DMSO and Et3N, as a dehydrating agent to obtain nitriles in excellent yield. This dehydration system was extended to a one-pot preparation of perfluoroimidates via volatile perfluoronitriles from perfluoroamides. Fifteen benzyl-type perfluoroimidates can be prepared in 70-90% yield as more stable imidates than the trichloro analogue. MPM- and DMPM-perfluoroimidates can be used to protect alcohols in place of the trichloroacetimidate with excellent chemical properties and in comparable yields. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Preparation and reaction of 4-methoxybenzyl (MPM) and 3,4-dimethoxybenzyl (DMPM) perfluoroimidates
  作者：Noriyuki Nakajima、Miho Saito、Makoto Ubukata

  DOI：10.1016/s0040-4039(98)01121-6

  日期：1998.7

  We have succeeded in one-pot preparation of perfluoroimidates at -78 degrees C by employing the dehydration of perfluoroamide under the "activated" dimethyl sulfoxide (DMSO) species followed by in situ nitrile trapping with alcohols. MPM and DMPM perfluoroimidates can be used to protect alcohols in place of the trichloroacetimidate with excellent chemical properties and in comparable yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Total synthesis and stereochemical reassignment of (+)-dolastatin 19, a cytotoxic marine macrolide isolated from Dolabella auricularia
  作者：Ian Paterson、Alison D. Findlay、Gordon J. Florence

  DOI：10.1016/j.tet.2007.01.048

  日期：2007.6

  the cytotoxic marine macrolide dolastatin 19 is proposed, together with its validation by completion of the first total synthesis. Key features of the highly stereocontrolled route include an asymmetric vinylogous Mukaiyama aldol reaction to simultaneously install both the remote C13 stereocenter and the C10–C11 (E)-trisubstituted olefin, two sequential 1,4-syn boron-mediated aldol reactions, and a late-stage

  利用构象分析和生物遗传学的考虑，提出了针对细胞毒性海洋大环内酯多拉汀19的修订构型分配，并通过完成第一个总合成对其进行了验证。高度立体控制的路线的主要特征包括不对称的乙烯基Mukaiyama羟醛反应，可同时安装远程C13立体中心和C10-C11（E）-三取代的烯烃，两个顺序的1,4-顺硼硼介导的羟醛反应，以及一个后期反应。阶段的α选择性Mukaiyama糖基化反应，以附加l-鼠李糖衍生的吡喃糖苷。