((dodecylthio)methoxy)triisopropylsilane | 1332721-91-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: ((dodecylthio)methoxy)triisopropylsilane
• 英文别名: Dodecylsulfanylmethoxy-tri(propan-2-yl)silane
• CAS: 1332721-91-1
• 化学式: C₂₂H₄₈OSSi
• 分子量: 388.774
• InChiKey: MBZQRNKYZABMCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.79
• 重原子数：
  25
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ((dodecylthio)methoxy)triisopropylsilane 在 2,6-二甲基吡啶 、 四丁基氟化铵 、 三乙胺 、 copper(ll) bromide 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 4.0h， 生成 tri(propan-2-yl)silyloxymethyl (4aS,7R,7aS)-7a-[(1S,3R)-1-methoxy-3-methyl-4-phenylmethoxybutyl]-5,7-dimethyl-6-oxo-2,2-di(propan-2-yl)-4,7-dihydro-[1,3,2]dioxasilino[5,4-b]pyrrole-4a-carboxylate
  参考文献：
  名称：

  Total Synthesis of Oxazolomycin A

  摘要：

  The first total synthesis of oxazolomycin A, a structurally novel oxazole polyene gamma-lactam/beta-lactone antibiotic, is described. Key features Include the stereocontrolled construction of the right-hand heterocyclic core by taking advantage of an In(III)-catalyzed Conia-ene type cyclization and the asymmetric synthesis of the left-hand segment starting with a Cinchona alkaloid-catalyzed cyclocondensation of an aldehyde with an acid chloride.

  DOI：

  10.1021/ol202306d
• 作为产物：
  描述：

  十二硫醇 在 咪唑 、 sodium methylate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 46.0h， 生成 ((dodecylthio)methoxy)triisopropylsilane
  参考文献：
  名称：

  Total Synthesis of Oxazolomycin A

  摘要：

  The first total synthesis of oxazolomycin A, a structurally novel oxazole polyene gamma-lactam/beta-lactone antibiotic, is described. Key features Include the stereocontrolled construction of the right-hand heterocyclic core by taking advantage of an In(III)-catalyzed Conia-ene type cyclization and the asymmetric synthesis of the left-hand segment starting with a Cinchona alkaloid-catalyzed cyclocondensation of an aldehyde with an acid chloride.

  DOI：

  10.1021/ol202306d

文献信息

• A New Method for the Protection of Carboxylic Acids with a Triisopropylsiloxymethyl Group
  作者：Hikaru Yoshimura、Kohei Eto、Keisuke Takahashi、Jun Ishihara、Susumi Hatakeyama

  DOI：10.1248/cpb.c12-00490

  日期：——

  An effective method for the protection of carboxylic acids with a triisopropylsiloxymethyl (TIPSOCH2) group is described. The reactions of various carboxylic acids with C12H25SCH2OTIPS in the presence of CuBr2, Et3N, and molecular sieves 4A afford the corresponding triisopropylsiloxymethyl esters in good yields.

  描述了一种有效的保护羧酸的方法，该方法使用三异丙基硅氧烷甲基（TIPSOCH2）基团。在CuBr2、Et3N和4A分子筛的存在下，各种羧酸与C12H25SCH2OTIPS反应，得到相应的三异丙基硅氧烷甲基酯，其产率良好。
• Synthesis of the Proposed Structure of Mohangic Acid C
  作者：Keisuke Takahashi、Shunya Kudo、Kiharu Kawamura、Taichi Kusakabe、Shoko Kikkawa、Isao Azumaya、Keisuke Kato

  DOI：10.1021/acs.orglett.2c01285

  日期：2022.5.13

  The proposed structure of mohangic acid C (3) was stereoselectively synthesized via a catalytic asymmetric aldol reaction to install a p-aminoacetophenone moiety, Marshall propargylation furnishing two stereocenters, and Cu-mediated Stille-type coupling to construct the whole framework of 3.

  通过催化不对称醛醇反应安装对氨基苯乙酮部分、提供两个立体中心的 Marshall 炔丙基化和 Cu 介导的 Stille 型偶联构建 3 的整个框架，立体选择性合成了所提出的 mohangic 酸 C ( 3 ) 结构。
• Stereoselective synthesis of the right-hand cores of 16-methylated oxazolomycins
  作者：Kohei Eto、Jun Ishihara、Susumi Hatakeyama

  DOI：10.1016/j.tet.2017.12.036

  日期：2018.2

  The right-hand heterocyclic cores of oxazolomycins having either 16R or 16S-methyl group configurations on the beta-lactones were stereoselectively synthesized from the common intermediate utilized for our previous syntheses of neooxazolomycin and oxazolomycin A. In addition, the right-hand segment required for the synthesis of KSM-2690 and lajollamycin members was also synthesized in a stereo-selective manner. (C) 2017 Elsevier Ltd. All rights reserved.