ethyl 4,6-di-O-benzyl-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside | 212192-83-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4,6-di-O-benzyl-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside
• 英文别名: ethyl-2,3-O-isopropylidene-4,6-di-O-benzyl-1-thio-α-D-mannopyranoside；(3aS,4R,6R,7R,7aS)-4-ethylsulfanyl-2,2-dimethyl-7-phenylmethoxy-6-(phenylmethoxymethyl)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran
• CAS: 212192-83-1
• 化学式: C₂₅H₃₂O₅S
• 分子量: 444.592
• InChiKey: SWSVMIRHQQJOHJ-URYYLNOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 4,6-di-O-benzyl-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 51.25h， 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：

  D-甘露糖 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 oil 为溶剂， 反应 4.5h， 生成 ethyl 4,6-di-O-benzyl-2,3-di-O-isopropylidene-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

文献信息

• 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.
• Disaccharide synthesis on a soluble hyperbranched polymer
  作者：Assen B Kantchev、Jon R Parquette

  DOI：10.1016/s0040-4039(99)01709-8

  日期：1999.11

  A hyperbranched star polymer was employed as a soluble support for disaccharide synthesis as a practical alternative to a dendrimer support. The large number of terminal groups present on the support permit very high loading levels to be possible. Polymer bound intermediates could be directly analyzed by MALDI-TOF mass spectrometry due to the presence of a photolabile linker that is cleaved by the MALDI-TOF laser. (C) 1999 Elsevier Science Ltd. All rights reserved.
• ——
  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.
• Oligosaccharide synthesis on a soluble, hyperbranched polymer support via thioglycoside activation
  作者：Eric Assen B. Kantchev、Scott J. Bader、Jon R. Parquette

  DOI：10.1016/j.tet.2005.06.101

  日期：2005.8

  The synthesis of linear and branched di-, tri- and tetramannosides on a commercially available hyperbranched polyester as a soluble, high loading support is described. Gil/cosylation products were isolated in 26-63% yield as mixtures of anomers after total hydrolytic degradation of the polymer. All polymer-bound intermediates were purified through simple extraction or precipitation. Solution phase NMR and MALDI-TOF were used to monitor the progress of the reaction directly on the hyperbranched polymer support. (c) 2005 Elsevier Ltd. All rights reserved.
• GLYCOMIMETIC COMPOUNDS AND METHODS TO INHIBIT INFECTION BY HIV
  申请人：MAGNANI John L.

  公开号：US20110251148A1

  公开（公告）日：2011-10-13

  Compounds, compositions and methods are provided for use to inhibit infection by human immunodeficiency virus (HIV). More specifically, the present invention relates to glycomimetic compounds that inhibit HIV infection, and uses thereof.

  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。