3-hexadecylthio-2-(hexadecylthiomethyl)propan-1-ol | 160533-88-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-hexadecylthio-2-(hexadecylthiomethyl)propan-1-ol
• 英文别名: 3-hexadecylsulfanyl-2-hexadecylsulfanylmethylpropan-1-ol；3-Hexadecylsulfanyl-2-(hexadecylsulfanylmethyl)propan-1-ol
• CAS: 160533-88-0
• 化学式: C₃₆H₇₄OS₂
• 分子量: 587.115
• InChiKey: MWJKTINJJDHZGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.6
• 重原子数：
  39
• 可旋转键数：
  35
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hexadecylthio-2-(hexadecylthiomethyl)propan-1-ol 在 potassium permanganate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 24.0h， 以63%的产率得到3-(hexadecane-1-sulfonyl)-2-(hexadecane-1-sulfonylmethyl)propionic acid
  参考文献：
  名称：

  Efficient Synthesis of Methanesulphonate-Derived Lipid Chains for Attachment of Proteins to Lipid Membranes

  摘要：

  We have developed an easy and flexible synthetic methodology to obtain lipid chains containing methanothiosulfonate terminal groups with the aim to attach them to natural proteins as functional groups. There are many proteins found in nature that are modified by lipids, and this is a key part of their function. For example, the prion protein is attached to the plasma membrane via a glycosylphosphatidylinositol (GPI) anchor, and this protein is thought to be the causative agent in diseases such as bovine spongiform encephalopathy (BSE; mad cow disease) and the human equivalent Creutzfeldt-Jakob disease. However, production of large amounts of protein in bacteria results in proteins that lack these lipid modifications. The lipid chains containing methanothiosulfonate terminal groups that we have synthesized here can be attached to these proteins through the thiol contained in the side chain of the cysteine residue, which can be incorporated into the protein sequence at the desired position.

  DOI：

  10.1080/00397910802213794
• 作为产物：
  描述：

  1-十六烷硫醇 、 1-溴-2-溴甲基-3-羟基丙烷 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以93%的产率得到3-hexadecylthio-2-(hexadecylthiomethyl)propan-1-ol
  参考文献：
  名称：

  2”-，3”-，4”-和6”-脱氧球菌病的双链双砜新糖脂的合成

  摘要：

  2-（三甲基甲硅烷基）乙基（Me3SiCH2CH2）2,3,6-三-O-苯甲酰基-4-O-（2,3-二-O-苯甲酰基-6-Op-甲氧基苄基-β-D-吡喃半乳糖基-β-用不同的2-，3-，4-或6-“脱氧-D-半乳糖”衍生物将D-吡喃葡萄糖苷糖基化，得到相应的脱氧三糖。除去保护基团得到Me3SiCH2CH2 2''-，3''- ，4''-和6''-脱氧globotriosides。通过半缩醛，将保护的Me3SiCH2CH2 globotriosides转化为相应的三氯乙酰亚胺酯，总收率为91-96％。3-（十六烷基磺酰基-2- [十六烷基磺酰基]的糖基化甲基]丙醇与三氯乙亚氨酸酯，然后除去保护基，得到标题新糖脂。

  DOI：

  10.1016/0008-6215(94)84006-7

文献信息

• Synthesis of double-chain bis-sulfone neoglycolipids of the 2″-, 3″-, 4″-, and 6″-deoxyglobotrioses
  作者：Zhang Zhiyuan、Göran Magnusson

  DOI：10.1016/0008-6215(94)84006-7

  日期：1994.9

  Me3SiCH2CH2 2''-, 3''-, 4''-, and 6''-deoxyglobotriosides. Transformation of the protected Me3SiCH2CH2 globotriosides into the corresponding trichloroacetimidates proceeded, via the hemiacetals, in 91-96% over-all yield. Glycosylation of 3-(hexadecylsulfonyl-2-[hexadecylsulfonyl)methyl]propanol with the trichloroacetimidates, followed by removal of protecting groups, gave the title neoglycolipids.

  2-（三甲基甲硅烷基）乙基（Me3SiCH2CH2）2,3,6-三-O-苯甲酰基-4-O-（2,3-二-O-苯甲酰基-6-Op-甲氧基苄基-β-D-吡喃半乳糖基-β-用不同的2-，3-，4-或6-“脱氧-D-半乳糖”衍生物将D-吡喃葡萄糖苷糖基化，得到相应的脱氧三糖。除去保护基团得到Me3SiCH2CH2 2''-，3''- ，4''-和6''-脱氧globotriosides。通过半缩醛，将保护的Me3SiCH2CH2 globotriosides转化为相应的三氯乙酰亚胺酯，总收率为91-96％。3-（十六烷基磺酰基-2- [十六烷基磺酰基]的糖基化甲基]丙醇与三氯乙亚氨酸酯，然后除去保护基，得到标题新糖脂。
• Efficient Synthesis of Methanesulphonate-Derived Lipid Chains for Attachment of Proteins to Lipid Membranes
  作者：Matthew R. Hicks、Atvinder K. Rullay、Rosa Pedrido、David H. Crout、Teresa J. T. Pinheiro

  DOI：10.1080/00397910802213794

  日期：2008.10.22

  We have developed an easy and flexible synthetic methodology to obtain lipid chains containing methanothiosulfonate terminal groups with the aim to attach them to natural proteins as functional groups. There are many proteins found in nature that are modified by lipids, and this is a key part of their function. For example, the prion protein is attached to the plasma membrane via a glycosylphosphatidylinositol (GPI) anchor, and this protein is thought to be the causative agent in diseases such as bovine spongiform encephalopathy (BSE; mad cow disease) and the human equivalent Creutzfeldt-Jakob disease. However, production of large amounts of protein in bacteria results in proteins that lack these lipid modifications. The lipid chains containing methanothiosulfonate terminal groups that we have synthesized here can be attached to these proteins through the thiol contained in the side chain of the cysteine residue, which can be incorporated into the protein sequence at the desired position.