octylthiotrimethylsilane | 79566-93-1

• 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: octylthiotrimethylsilane
• 英文别名: Octyl trimethyl sulfide；Trimethyl(octylsulfanyl)silane
• CAS: 79566-93-1
• 化学式: C₁₁H₂₆SSi
• 分子量: 218.479
• InChiKey: ZHWFXQQQQJIVQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  octylthiotrimethylsilane 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 360.0h， 生成 octyl 2-azido-2-deoxy-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of octyl S-glycosides of tri- to pentasaccharide fragments related to the GPI anchor of Trypanosoma brucei

  摘要：

  The three oligosaccharide octyl-S-glycosides Man-alpha 1,6-Man-alpha 1,4-GlcNH(2)-alpha 1,S-Octyl (19), Man-alpha 1,6-(Gal-alpha 1,3)Man-alpha 1,4-GlcNH(2)-alpha 1,S-Octyl (27) and Man-alpha 1,2-Man-alpha 1,6-(Gal-alpha 1,3)Man-alpha 1,4-GlcNH(2)-alpha 1,S-Octyl (37), related to the GPI anchor of Trypanosoma brucei were prepared by a stepwise and block-wise approach from octyl 2-azido-2-deoxy-3,6-di-O-benzyl-1-thio-alpha-D-glucopyranoside (8) and octyl 2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-1-thio-alpha-D-mannopyransoside (9). Glucosamine derivative 8 was obtained from 1,3,4,6-tetra-O-acetyl-2-azido-2-desoxy-beta-D-glucopyranose (1) in five steps. Mannoside 9 was converted into the corresponding imidate 12 and coupled with 8 to give disaccharide octyl-S-glycoside 13 which was further mannosylated to afford trisaccharide 19 upon deprotection. Likewise, mannoside 9 was galactosylated, converted into the corresponding imidate and coupled with 8 to give trisaccharide 25. Mannosylation of the latter afforded tetrasaccharide 27 upon deprotection. Condensation of 25 with disaccharide imidate 35 gave, upon deprotection of the intermediates, the corresponding pentasaccharide octyl-S-glycoside 37. Saccharides 19, 27 and 37 are suitable substrates for studying the enzymatic glycosylation pattern of the GPI anchor of T. brucei. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.08.001
• 作为产物：
  描述：

  三甲基氯硅烷 、 1-辛硫醇 在 sodium 作用下， 以 正己烷 为溶剂， 反应 2.0h， 以67%的产率得到octylthiotrimethylsilane
  参考文献：
  名称：

  Synthesis of octyl S-glycosides of tri- to pentasaccharide fragments related to the GPI anchor of Trypanosoma brucei

  摘要：

  The three oligosaccharide octyl-S-glycosides Man-alpha 1,6-Man-alpha 1,4-GlcNH(2)-alpha 1,S-Octyl (19), Man-alpha 1,6-(Gal-alpha 1,3)Man-alpha 1,4-GlcNH(2)-alpha 1,S-Octyl (27) and Man-alpha 1,2-Man-alpha 1,6-(Gal-alpha 1,3)Man-alpha 1,4-GlcNH(2)-alpha 1,S-Octyl (37), related to the GPI anchor of Trypanosoma brucei were prepared by a stepwise and block-wise approach from octyl 2-azido-2-deoxy-3,6-di-O-benzyl-1-thio-alpha-D-glucopyranoside (8) and octyl 2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-1-thio-alpha-D-mannopyransoside (9). Glucosamine derivative 8 was obtained from 1,3,4,6-tetra-O-acetyl-2-azido-2-desoxy-beta-D-glucopyranose (1) in five steps. Mannoside 9 was converted into the corresponding imidate 12 and coupled with 8 to give disaccharide octyl-S-glycoside 13 which was further mannosylated to afford trisaccharide 19 upon deprotection. Likewise, mannoside 9 was galactosylated, converted into the corresponding imidate and coupled with 8 to give trisaccharide 25. Mannosylation of the latter afforded tetrasaccharide 27 upon deprotection. Condensation of 25 with disaccharide imidate 35 gave, upon deprotection of the intermediates, the corresponding pentasaccharide octyl-S-glycoside 37. Saccharides 19, 27 and 37 are suitable substrates for studying the enzymatic glycosylation pattern of the GPI anchor of T. brucei. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.08.001

文献信息

• Visible light driven photoredox/nickel-catalyzed stereoselective synthesis of Z- or E-vinyl thioethers from thiosilane and terminal alkynes
  作者：Hongqiang Liu、Wenjing Li、Xia Xu、Meiding Yang、Deman Han、Xiujuan Yang

  DOI：10.1039/d4ob00652f

  日期：——

  A new method for the synthesis of anti-Markovnikov Z- or E-vinyl thioethers from thiosilane and terminal alkynes under visible-light-induced photoredox/nickel dual catalysis conditions is described. With a judicious choice of a simple nickel catalyst and a ligand, this strategy enables efficient and divergent access to both Z- or E-vinyl thioethers from the same set of simple starting materials. Notably

  描述了一种在可见光诱导的光氧化还原/镍双催化条件下由硫硅烷和末端炔合成反马可夫尼科夫Z-或E-乙烯基硫醚的新方法。通过明智地选择简单的镍催化剂和配体，该策略能够从同一组简单的起始材料中高效且多样化地获得Z-或E-乙烯基硫醚。值得注意的是，该方法不含有气味的硫醇，并且与官能团和底物范围具有出色的相容性。
• Preparation of<i>S</i>-Alkyl and<i>S</i>-Aryl Thiocarboxylates from Acyl Chlorides and Trimethylsilyl Thioethers
  作者：John J. Talley

  DOI：10.1055/s-1981-29522

  日期：——
• Hole Transfer Dynamics from a CdSe/CdS Quantum Rod to a Tethered Ferrocene Derivative
  作者：Kartick Tarafder、Yogesh Surendranath、Jacob H. Olshansky、A. Paul Alivisatos、Lin-Wang Wang

  DOI：10.1021/ja500936n

  日期：2014.4.2

  Hole transfer between a CdSe/CdS core/shell semiconductor nanorod and a surface-ligated alkyl ferrocene is investigated by a combination of ab initio quantum chemistry calculations and electrochemical and time-resolved photoluminescence measurements. The calculated driving force for hole transfer corresponds well with electrochemical measurements of nanorods partially ligated by 6-ferrocenylhexanethiolate. The calculations and the experiments suggest that single step hole transfer from the valence band to ferrocene is in the Marcus inverted region. Additionally, time-resolved photoluminescence data suggest that two-step hole transfer to ferrocene mediated by a deep trap state is unlikely. However, the calculations also suggest that shallow surface states of the CdS shell could play a significant role in mediating hole transfer as long as their energies are close enough to the nanorod highest occupied molecular orbital energy. Regardless of the detailed mechanism of hole transfer, our results suggest that holes may be extracted more efficiently from well-passivated nanocrystals by reducing the energetic driving force for hole transfer, thus minimizing energetic losses.
• TALLEY F. F., SYNTHESIS (BRD), 1981, NO 7, 549
  作者：TALLEY F. F.

  DOI：——

  日期：——