ethyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside | 151669-30-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside
• 英文别名: ethyl 2,3-O-isopropylidene-1-thio-α-D-mannopyranoside；ethyl-2,3-O-isopropylidene-1-thio-α-D-mannopyranoside
• CAS: 151669-30-6
• 化学式: C₁₁H₂₀O₅S
• 分子量: 264.343
• InChiKey: JSZDTPZQDWUANA-FHNUBNKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.34
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside 在 potassium tert-butylate 、 四丁基溴化铵 、 水 、 sodium hydride 、 溶剂黄146 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 oil 为溶剂， 反应 51.5h， 生成 Ethyl 3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  GLYCOMIMETIC COMPOUNDS AND METHODS TO INHIBIT INFECTION BY HIV

  摘要：

  提供了用于抑制人类免疫缺陷病毒（HIV）感染的化合物、组合物和方法。更具体地，本发明涉及抑制HIV感染的糖类模拟化合物及其用途。

  公开号：

  US20110251148A1
• 作为产物：
  描述：

  S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside 在 sodium methylate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 ethyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  通过1,2-乙基（苯基）2,3-原酸酯-1-硫代-α-甘露吡喃糖苷的1,2-迁移和同时糖苷化立体选择性合成2-S-乙基（苯基）-2-硫代-β-吡喃葡萄糖苷

  摘要：

  摘要在TMSOTf作用下，乙基（苯基）2，3-原酸酯-1-硫代α-d-和1-甘露吡喃糖苷的1,2-迁移和同时的糖基化反应很容易得到相应的2-S-乙基（苯基）- 2-硫代-β-吡喃葡萄糖苷，是2-脱氧-阿拉伯糖基-己吡喃糖苷（2-脱氧-β-吡喃葡萄糖苷）的现成前体。

  DOI：

  10.1016/s0008-6215(01)00124-0

文献信息

• A novel strategy towards the synthesis of orthogonally functionalised 4-aminoglycosides
  作者：Leendert J. van den Bos、Jeroen D.C. Codée、Jacques H. van Boom、Herman S. Overkleeft、Gijsbert A. van der Marel

  DOI：10.1039/b309823k

  日期：——

  A tethered nucleophilic substitution strategy for the stereoselective introduction of axially oriented amino functions on suitably protected gluco- and mannopyranosides is presented. The obtained oxazine is a versatile building block, which after some manipulation, could be used in the construction of highly functionalised oligosaccharides.

  presented. 本文提出了一种系绳亲核取代策略，用于在适当保护的葡萄糖和甘露糖吡喃糖上立体选择性地引入轴向氨基功能。所获得的噁唑啉是一种多功能的构建块，经过一些操作后，可以用于构建高度功能化的寡糖。
• Iodonium ion-assisted synthesis of tetrameric fragments corresponding to the cell wall phenolic glycolipids of Mycobacterium kansasii serovars II and IV
  作者：Korien Zegelaar-Jaarsveld、Howard I. Duynstee、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1016/0040-4020(96)00034-8

  日期：1996.3

  The spacer-containing tetramers 3 and 4, derivatives of the phenolic glycolipids of Mycobacterium kansasii serovars II and IV were prepared by iodonium ion-mediated mannosylation of trimeric acceptor 4-[2-(benzyloxycarbonylamino)ethyl]phenyl (2) with ethyl 1-thio-d-mannopyranoside donors 7, 13, and 24. In addition, the glycosylating properties of donors 7, 13, 24, 29–31, each containing a different

  含间隔基的四聚体3和4，堪萨斯分枝杆菌血清型II和IV的酚糖脂衍生物是通过碘离子介导的三聚体受体4- [2-（苄氧基羰基氨基）乙基]苯基（2）与1-乙基的甘露糖基化反应制得的。硫代d-D-吡喃甘露糖苷供体7，13，和24。此外，供体的糖基化特性7，13，24，29-31，每个包含一个不同的保护基团在2位，通过用模型受体执行缩合检查18（L）和其对映体18（d）。
• Synthesis of and molecular dynamics simulations on a tetrasaccharide corresponding to the repeating unit of the capsular polysaccharide from Salmonella enteritidis
  作者：Johan D. M. Olsson、Jens Landström、Jerk Rönnols、Stefan Oscarson、Göran Widmalm

  DOI：10.1039/b823428k

  日期：——

  Syntheses of two oligosaccharides as methyl glycosides related to the repeating unit of S. enteritidis capsular polysaccharide (CPS) are presented. The trisaccharide corresponds to the backbone of the CPS whereas the tetrasaccharide is a model for the repeating unit which has a branched structure. Molecular dynamics simulations investigating their flexibility and dynamics revealed that the oligosaccharides

  提出了两种寡糖的合成，它们是与肠炎沙门氏菌荚膜多糖（CPS）的重复单元有关的甲基糖苷。三糖对应于CPS的主链，而四糖是具有分支结构的重复单元的模型。分子动力学模拟研究其灵活性和动力学表明，寡糖填充了几种构象状态，并表明构象平均应用于描述可及的构象空间。
• Synthesis of A Di-and a Trisaccharide Related to the Antigen from<i>Klebsiella</i>Type 43
  作者：Sumita Sarbajna、Anup K. Misra、Nirmolendu Roy

  DOI：10.1080/00397919808004824

  日期：1998.7

  Starting from D-galactose, D-mannose and D-glucose methyl alpha-D-galactopyranosyl-(1-->3)-alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranoside and allyl beta-D-mannopyranosyl-(1-->4)-beta-D-glucopyranosyl uronate were synthesised in a highly stereoselective manner.
• ——
  作者：Gregor Lemanski、Thomas Ziegler

  DOI：10.1002/1522-2675(20001004)83:10<2655::aid-hlca2655>3.0.co;2-u

  日期：2000.10.4

  A series of prearranged glycosides 5, 17, 23, 28, 37 and 41, having a benzyl-protected 1-thiomannosyl donor linked through its positions 2, 3, 4 and 6 via succinate and malonate tethers, respectively, to positions 2, 3, and 6 of a benzyl glucopyranoside acceptor, were prepared by condensation of the respective mannosyl succinates and malonates with suitably protected benzyl glucopyranosides. The prearranged glycosides were intramolecularly coupled under various conditions to give the corresponding, tethered (1 --> 4)-linked disaccharides The yields and anomer ratios of the products of these couplings were interpreted in terms of the thermodynamic stability of the resulting disaccharides. In the case of prearranged glycoside 17, having positions 3 of both the donor and the acceptor linked by a succinate tether, a strong dependence of the diastereoselectivity of the intramolecular glycosylation on the activation procedure was observed. All other cases did not show a significant dependence of the outcome of the anomeric configuration in intramolecular glycosylation on the activation procedure or the solvent.