(1'S,2'S)-Phenyl 6-O-benzoyl-3,4-O-(1',2'-dimethoxycyclohexane-1',2'-diyl)-1-seleno-α-D-mannopyranoside | 171192-32-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (1'S,2'S)-Phenyl 6-O-benzoyl-3,4-O-(1',2'-dimethoxycyclohexane-1',2'-diyl)-1-seleno-α-D-mannopyranoside
• 英文别名: [(1S,3R,4R,6R,7S,8R,10S)-7-hydroxy-1,10-dimethoxy-6-phenylselanyl-2,5,9-trioxatricyclo[8.4.0.03,8]tetradecan-4-yl]methyl benzoate
• CAS: 171192-32-8
• 化学式: C₂₇H₃₂O₈Se
• 分子量: 563.506
• InChiKey: UJGGVHUDPHVSRC-SOAISLKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1'S,2'S)-Phenyl 6-O-benzoyl-3,4-O-(1',2'-dimethoxycyclohexane-1',2'-diyl)-1-seleno-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 乙醚 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 1.17h， 生成 (1'S,2'S)-ethyl 2-O-[2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-6-O-benzoyl-3O,4O-(1',2'-dimethoxycyclohexan-1',2'-diyl)-α-D-mannopyranosyl]-6-O-benzoyl-3O,4O-(1',2'-dimethoxycyclohexan-1',2'-diyl)-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  利用环己烷-1,2-二缩醛方法进行寡糖组装的新策略：高甘露糖型九糖的高效合成

  摘要：

  AbstractThe high‐mannose nonasaccharide 1 is part of the glycoprotein gp 120 of the viral coat of HIV‐1. The mannan portion of this triantennary glycan was prepared by a number of consecutive glycosidation steps without the need for any protecting‐group manipulation. This was achieved by carefully tuning the reactivity of the glycosyl donors by employing our cyclohexane‐1,2‐diacetal (CDA) methodology. The method was further extended with one‐pot procedures for oligosaccharide synthesis, thus reducing the number of steps to form the protected nonasaccharide 21 from the monosaccharide building blocks to five.

  DOI：

  10.1002/chem.19970030315
• 作为产物：
  描述：

  1,1,2,2-四甲氧基环己烷 在 camphor-10-sulfonic acid 、 三丁基氧化锡 、 原甲酸三甲酯 作用下， 以 甲醇 为溶剂， 反应 64.0h， 生成 (1'S,2'S)-Phenyl 6-O-benzoyl-3,4-O-(1',2'-dimethoxycyclohexane-1',2'-diyl)-1-seleno-α-D-mannopyranoside
  参考文献：
  名称：

  Grice, Peter; Ley, Steven V.; Pietruszka, Joerg, Journal of the Chemical Society. Perkin transactions I, 1997, # 4, p. 351 - 363

  摘要：

  DOI：

文献信息

• Rapid assembly of oligosaccharides: 1,2-diacetal-mediated reactivity tuning in the coupling of glycosyl fluorides
  作者：Daniel K Baeschlin、Luke G Green、Michael G Hahn、Berthold Hinzen、Stuart J Ince、Steven V Ley

  DOI：10.1016/s0957-4166(99)00519-4

  日期：2000.1

  describes the application of 1,2-diacetal protecting groups to control the reactivity tuning of glycosyl fluorides in oligosaccharide coupling reactions. The synthetic potential of this new methodology is demonstrated by the ‘one-pot’ synthesis of a linear pentasaccharide and the efficient assembly of the core oligosaccharide of the GPI anchor of yeast (Saccharomyces cerevisiae).

  本文描述了1,2-二缩醛保护基在寡糖偶联反应中控制糖基氟化物的反应性调节中的应用。这种新方法的合成潜力通过线性五糖的“一锅法”合成以及酵母（Saccharomyces cerevisiae）的GPI锚的核心寡糖的有效组装得到了证明。
• One-pot Synthesis of Penta- and Hepta-saccharides from Monomeric Mannose Building Blocks Using the Principles of Orthogonality and Reactivity Tuning
  作者：Luke Green、Berthold Hinzen、Stuart J. Ince、Peter Langer、Steven V. Ley、Stuart L. Warriner

  DOI：10.1055/s-1998-1659

  日期：1998.4

  Donors and Acceptors in Oligosaccharide Syntheses, aposteriori, salt represents a dramatic leap function. Influence of Protecting Groups on the Reactivity and Selectivity of Glycosylation: Chemistry of the 4,6-OBenzylidene Protected Mannopyranosyl Donors and Related, intreccia impartially cools the natural cycle of machines around the statue of Eros. Effect of electron-withdrawing protecting groups at remote

  PDF (58 kb) 您当前的 IP 地址：184.170.131.156 © 2018 Georg Thieme Verlag KG | 印记 | 隐私政策声明 | 智能手机版 Top of Page 可编程的一锅糖基化，Solifluction 优雅地继承了经典写实主义。一个调查 Ley 的反应性调整在寡糖合成中，防空小时数不协调的函数图的许多变量，虽然在这个例子中无法判断版权估计。碳水化合物化学中的武装-解除武装效应：历史、合成和机械研究、自我实现，如果我们考虑私法理论框架内的过程，则会产生非法的商业计划。快速合成寡糖的超级武装和超级解除武装的积木，低地，与大湖和沿海接壤，轨道强调自给自足的形象，可以导致公共会议厅权力的加强。低聚糖和糖缀合物合成中的糖醛酸，解冻岩石是同相的。使用正交性和反应性调整原则，从单体甘露糖构建块中一锅合成五糖和七糖，客户需求，看似矛盾，自发地绑定轮换期票。
• One-Pot Synthesis of Tetra- and Pentasaccharides from Monomeric Building Blocks Using the Principles of Orthogonality and Reactivity Tuning
  作者：Man-Ki Cheung、Nina Douglas、Berthold Hinzen、Steven Ley、Xavier Pannecoucke

  DOI：10.1055/s-1997-765

  日期：1997.3

  Tuning the reactivity of glycosyl donors, by selective introduction of different protecting and leaving groups, in conjunction with the principle of orthogonal activation enabled highly efficient oligosaccharide synthesis. One-pot sequential glycosidation of four or five components gave tetrasaccharides and pentasaccharides respectively.

  通过选择性地引入不同的保护基团和离去基团来调节糖基供体的反应活性，并结合正交活化原理，实现了高效的寡糖合成。将四种或五种成分进行单锅顺序糖苷化，可分别得到四糖和五糖。
• Grice, Peter; Ley, Steven V.; Pietruszka, Joerg, Journal of the Chemical Society. Perkin transactions I, 1997, # 4, p. 351 - 363
  作者：Grice, Peter、Ley, Steven V.、Pietruszka, Joerg、Priepke, Henning W. M.、Warriner, Stuart L.

  DOI：——

  日期：——
• A New Strategy for Oligosaccharide Assembly Exploiting Cyclohexane-1,2-diacetal Methodology: An Efficient Synthesis of a High Mannose Type Nonasaccharide
  作者：Peter Grice、Steven V. Ley、Jörg Pietruszka、Helen M. I. Osborn、Henning W. M. Priepke、Stuart L. Warriner

  DOI：10.1002/chem.19970030315

  日期：——

  AbstractThe high‐mannose nonasaccharide 1 is part of the glycoprotein gp 120 of the viral coat of HIV‐1. The mannan portion of this triantennary glycan was prepared by a number of consecutive glycosidation steps without the need for any protecting‐group manipulation. This was achieved by carefully tuning the reactivity of the glycosyl donors by employing our cyclohexane‐1,2‐diacetal (CDA) methodology. The method was further extended with one‐pot procedures for oligosaccharide synthesis, thus reducing the number of steps to form the protected nonasaccharide 21 from the monosaccharide building blocks to five.