2-hydroxyethyl 2',3',4',6'-tetra-O-acetyl-1'-thio-β-D-galactopyranoside | 132156-08-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-hydroxyethyl 2',3',4',6'-tetra-O-acetyl-1'-thio-β-D-galactopyranoside
• 英文别名: 2-hydroxyethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside；[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(2-hydroxyethylsulfanyl)oxan-2-yl]methyl acetate
• CAS: 132156-08-2
• 化学式: C₁₆H₂₄O₁₀S
• 分子量: 408.427
• InChiKey: MXYFIWVKSKVWBH-CWVYHPPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  160
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-hydroxyethyl 2',3',4',6'-tetra-O-acetyl-1'-thio-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以83%的产率得到cis-4-(4-methoxyphenyl)-3-phenoxy-azetidin-2-one
  参考文献：
  名称：

  Preparation and Reactions of 2-Chloroethyl 1-Thio-β-D-glycopyranosides Derived from D-Galactose, D-Glucose, and 2-Acetamido-2-deoxy-D-glucose

  摘要：

  D-半乳糖 和D-葡萄糖 构型的氯乙基1-硫代-β-D-吡喃糖苷 5a-5c 通过用1-溴-2-氯乙烷烷基化相应的1-硫代-β-D-己糖吡喃糖 3a-3c，然后去乙酰化制备而成。起始的1-硫代-β-D-己糖吡喃糖是通过乙酰化的吡喃糖卤代物 经由 异硫脲盐获得的。实验证明，氯乙基硫代糖苷 5a-5c 在水溶液中发生水解，生成2-羟乙基硫代糖苷 6a-6c 和还原性己糖，并且这种水解是通过环硫銨盐进行的。水解过程通过 ¹H 和 ¹³C NMR光谱进行监测。在含酚或苯胺的1%碳酸钠水溶液中，硫代糖苷 5a-5c 除了产生上述水解产物外，还生成苯氧乙基和苯胺基乙基硫代糖苷 9a、10a和 9b、10b。

  DOI：

  10.1135/cccc19961489
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-1-硫代-BETA-D-吡喃半乳糖 、 2-溴乙醇 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 以86%的产率得到2-hydroxyethyl 2',3',4',6'-tetra-O-acetyl-1'-thio-β-D-galactopyranoside
  参考文献：
  名称：

  捕获标签释放：天然酶小分子标记的策略

  摘要：

  捕获，标记和释放：我们报告了一种利用小分子Staudinger连接的偶联和片段化特性来标记小分子天然酶的方法。作为原理的证明，该策略被应用于β-半乳糖苷酶。重要的是，抑制剂在最后一步的释放恢复了酶的活性。

  DOI：

  10.1002/cbic.201600267

文献信息

• Water-soluble cholesteryl-containing phosphorothioate monogalactosides: synthesis, properties, and use in lowering blood cholesterol by directing plasma lipoproteins to the liver
  作者：Harlof C. P. F. Roelen、Martin K. Bijsterbosch、Hille F. Bakkeren、Theo J. C. Van Berkel、Herman J. M. Kempen、Marinus Buytenhek、Gijs A. Van der Marel、Jacques H. Van Boom

  DOI：10.1021/jm00107a024

  日期：1991.3

  The synthesis of several monogalactoside-terminated phosphorothiolated cholesteryl derivatives is described. Monogalactosyl derivatives are coupled by phosphorothiolation to cholesterol by using ethylene glycol units as hydrophilic spacer moieties. The resulting compounds are easily soluble in water. Upon addition of such solutions to human serum (to 2 mM final concentration) the compounds are readily incorporated into lipoproteins. Isolated low-density lipoprotein (LDL) and high-density lipoprotein (HDL), preloaded with the compounds, are rapidly cleared from the circulation by the liver. The hepatic association is blocked by N-acetylgalactosamine, which indicates that galactose-specific recognition sites are responsible for the increased liver uptake. The plasma clearance and hepatic uptake of LDL loaded with the compounds is substantially higher (about 2-fold) than clearance and uptake of HDL containing the compounds. The selectivity of the effects of monogalactoside-terminated phosphorothiolated cholesteryl derivatives on the in vivo behavior of LDL as compared to that of HDL indicates that these compounds might be used to lower specifically LDL levels in patients with a high LDL-cholesterol level.