Methanesulfonic acid (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester | 73111-13-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methanesulfonic acid (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester
• 英文别名: [(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl methanesulfonate
• CAS: 73111-13-4
• 化学式: C₂₉H₃₄O₈S
• 分子量: 542.65
• InChiKey: YNEHHLPWLJUARD-RQKPWJHBSA-N

物化性质

• 沸点：
  671.7±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester 生成 methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  具有碱性假三糖结构的α-葡糖苷酶抑制剂淀粉抑制素（XG）的合成

  摘要：

  碱性假三糖（1是构成几种微生物来源的α-葡萄糖苷酶抑制剂的通用组成部分）是通过偶联两个合成子合成的：手性环己基卤化物（11）和4'-氨基-4'-脱氧二糖（14 ）。

  DOI：

  10.1016/s0040-4039(00)85830-x
• 作为产物：
  描述：

  甲基-6-O-三苯基甲基-alpha-D-吡喃葡萄糖苷 在 三氟化硼乙醚 、 sodium hydride 、 三乙胺 作用下， 反应 4.0h， 生成 Methanesulfonic acid (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Evaluation of potential Myt1 kinase inhibitors by TR-FRET based binding assay

  摘要：

  In the human cell cycle, the Myt1 kinase is a crucial regulator of the G2/M transition. Because this membrane-associated kinase is hard to obtain and assay, there is a distinct lack of data so far. Here we report the derivatization of a glycoglycerolipid which was shown previously to be active in a Myt1 activity assay. These compounds were tested in a binding assay together with a set of common kinase inhibitors against a full-length Myt1 expressed in a human cell line. Dasatinib exhibited nanomolar affinity whereas broad coverage inhibitors such as sunitinib and staurosporine derivatives did not show any effect. We also carried out docking studies for the most potent compounds allowing further insights into the inhibitor interaction of this kinase. The glycoglycerolipids showed no significant effects in the binding assay, endorsing the idea of a mechanism of action distant from the active site. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.007

文献信息

• A new way to do an old reaction: highly efficient reduction of organic azides by sodium iodide in the presence of acidic ion exchange resin
  作者：Kajitha Suthagar、Antony J. Fairbanks

  DOI：10.1039/c6cc08574a

  日期：——

  Organic azides are readily reduced to the corresponding amines by treatment with sodium iodide in the presence of acidic ion exchange resin. The process, optimal when performed at 40 oC...

  通过在酸性离子交换树脂的存在下用碘化钠处理，有机叠氮化物容易还原为相应的胺。该过程在40 oC下执行时最佳...
• Synthesis and in Vitro Evaluation of Inhibitors of Intestinal Cholesterol Absorption
  作者：Lisbet Kværnø,、Moritz Werder、Helmut Hauser、Erick M. Carreira

  DOI：10.1021/jm050422p

  日期：2005.9.1

  We have utilized our recently developed in vitro assay to address two key questions in the design of small-molecule cholesterol absorption inhibitors using ezetimibe, the only drug yet approved for the inhibition of cholesterol absorption in the small intestine, as a starting point: (1) the role of glycosylation and (2) the importance of the beta-lactam scaffold of ezetimibe for inhibitory activity

  我们已经利用我们最近开发的体外测定法来解决使用依泽替米贝设计小分子胆固醇吸收抑制剂的两个关键问题，依泽替米贝是唯一尚未批准的抑制小肠胆固醇吸收的药物，作为出发点：（1 ）糖基化的作用，以及（2）依泽替米贝的β-内酰胺支架对于抑制活性的重要性。合成了多种依泽替米贝的不可水解酚类糖苷，并使用刷状缘膜囊泡测定法证明是胆固醇吸收的活性抑制剂。类似的氮杂环丁烷提供了体外使用各种抑制剂的途径，这表明依泽替米贝的β-内酰胺仅用作适当地定位所需取代基的环骨架。
• Novel hypocholesterolemic compounds
  申请人：Lipideon Biotechnology AG

  公开号：EP1522541A1

  公开（公告）日：2005-04-13

  The present invention relates to novel hypocholesterolemic compounds of formula I useful in the treatment and prevention of atherosclerosis and for the reduction of cholesterol levels as well as to pharmaceutical compositions comprising said compounds alone or in combination with other active agents

  本发明涉及一种新型降胆固醇化合物，其化学式为I，可用于治疗和预防动脉粥样硬化，降低胆固醇水平，以及包含该化合物单独或与其他活性剂组合的药物组合物。
• Synthesis of non-glycosidically linked selenoether pseudodisaccharides
  作者：Viviane Fournière、Ian Cumpstey

  DOI：10.1016/j.tetlet.2010.02.064

  日期：2010.4

  Non-glycosidically linked disaccharide mimetics with a selenoether functionality linking the two monosaccharide residues have been synthesised. Protected Glc(Se3–3)Glc, Glc(Se3–6)Glc and Glc(Se3–6)Man structures were obtained. Selenium was introduced by displacement of carbohydrate sulfonates with a selenobenzoate anion. Conversion into diselenides by methanolysis of the benzoate and aerial oxidation

  已经合成了具有将两个单糖残基连接的硒醚官能团的非糖苷连接的二糖模拟物。获得了保护的Glc（Se 3–3）Glc，Glc（Se 3–6）Glc和Glc（Se 3–6）Man结构。通过用硒代苯甲酸酯阴离子置换碳水化合物磺酸盐来引入硒。通过苯甲酸酯的甲醇分解和空中氧化转化为二硒代，随后将二硒代还原为亚硒酸酯，并在S N 2反应中原位置换第二种碳水化合物磺酸盐以得到硒醚。还以去保护的形式获得了Glc（Se 3–3）Glc和Glc（Se 3–6）Glc。
• Carbohydrate Sulfonyl Chlorides for Simple, Convenient Access to Glycoconjugates
  作者：Lisbet Kværnø,、Moritz Werder、Helmut Hauser、Erick M. Carreira

  DOI：10.1021/ol0502127

  日期：2005.3.1

  [GRAPHICS]The use of carbohydrate sulfonyl chlorides is introduced as a new, facile glycoconjugation method which could find broad applications. We demonstrate the approach by synthesizing a number of glycosylated cholesterol absorption inhibitors which display high inhibitory efficacies in our recently established in vitro assay. Furthermore, we highlight an advantage of the electron-withdrawing nature of the suffonyl linkage which allowed the synthesis of otherwise unstable azetidine conjugates.