phenyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside | 849938-02-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6R)-6-phenoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanol
• CAS: 849938-02-9
• 化学式: C₃₃H₃₄O₆
• 分子量: 526.629
• InChiKey: HSNXRAGPIRAXPR-ZPZOKNLESA-N

物化性质

• 沸点：
  662.0±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 在 2-碘酰基苯甲酸 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  气相和溶液中的AC-联糖模拟物：二糖Manα（1,6）-C-ManαOPh的合成和构型

  摘要：

  碳的效果是微妙的，但甜：在新合成的柔性C-联动Ç α-糖基模拟物，Manα（1,6） - c ^ -ManαOPh允许OH  π键合，无论是在气相中和在水溶液中。O联二糖中不存在这种相互作用（见图）。

  DOI：

  10.1002/chem.200802179
• 作为产物：
  描述：

  苯基 alpha-D-吡喃甘露糖苷 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 86.0h， 生成 phenyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Building Up Key Segments of N-Glycans in the Gas Phase:  Intrinsic Structural Preferences of the α(1,3) and α(1,6) Dimannosides

  摘要：

  The intrinsic conformer specific vibrational spectra of two important subunits of the core pentasaccharide of Winked glycans, the alpha(1,3) and alpha(1,6) dimannosides, have been recorded in the gas phase. Coupling these measurements with a computational exploration of their conformational landscapes has enabled their conformational assignment and has identified characteristic vibrational signatures associated with particular conformational families-including those that do or do not display inter-ring hydrogen bonding across the glycosidic linkage. In addition, the IR spectra of the monosaccharide moieties provide benchmarks, through which the conformational assignments can be refined. This introduces a general concept of modularity and secondary structure in oligosaccharides-essential for the success of similar studies on larger oligosaccharides in the future.

  DOI：

  10.1021/ja055891v

文献信息

• Glycal Scavenging in the Synthesis of Disaccharides Using Mannosyl Iodide Donors¹
  作者：Son N. Lam、Jacquelyn Gervay-Hague

  DOI：10.1021/jo0478609

  日期：2005.3.1

  High mannose glycans composed of α (1→2) and α (1→6) branched sugars are important components of the HIV-associated envelope glycoprotein, gp120. These substructures can be efficiently prepared in solution from glycosyl iodide precursors requiring only a slight excess of the iodide donor, which offers advantages over solid-phase methods that require more than 5 equiv of donor. During the reaction,

  由α（1→2）和α（1→6）分支糖组成的高甘露糖聚糖是与HIV相关的包膜糖蛋白gp120的重要组成部分。这些亚结构可以从糖基碘化物前体的溶液中有效地制备，该糖基碘化物前体仅需要稍微过量的碘化物供体，这比需要多于5当量的供体的固相方法具有优势。在反应过程中，过量的碘化物转化为不容易与所需二糖分离的糖基。为了克服这个困难，已经开发了一种相移方法，该相移方法依赖于由糖基的氧化产生的1,2脱水糖的亲核拦截。
• Glycosyl iodides. History and recent advances
  作者：Peter J. Meloncelli、Alan D. Martin、Todd L. Lowary

  DOI：10.1016/j.carres.2009.02.032

  日期：2009.6

  The use of glycosyl iodides as an effective method for the preparation of glycosides has had a recent resurgence in carbohydrate chemistry, despite its early roots in which these species were believed to be of limited use. Renewed interest in these species as glycosylating agents has been spurred by their demonstrated utility in the stereoselective preparation of O-glycosides, and other glycosylic compounds. This review provides a brief historical account followed by an examination of the use of glycosyl iodides in the synthesis of oligosaccharicles and other glycomimetics, including C-glycosylic compounds, glycosyl azides and N-glycosides. (C) 2009 Elsevier Ltd. All rights reserved.
• Building Up Key Segments of <i>N</i>-Glycans in the Gas Phase:  Intrinsic Structural Preferences of the α(1,3) and α(1,6) Dimannosides
  作者：Pierre Çarçabal、Isabel Hünig、David P. Gamblin、Bo Liu、Rebecca A. Jockusch、Romano T. Kroemer、Lavina C. Snoek、Anthony J. Fairbanks、Benjamin G. Davis、John P. Simons

  DOI：10.1021/ja055891v

  日期：2006.2.1

  The intrinsic conformer specific vibrational spectra of two important subunits of the core pentasaccharide of Winked glycans, the alpha(1,3) and alpha(1,6) dimannosides, have been recorded in the gas phase. Coupling these measurements with a computational exploration of their conformational landscapes has enabled their conformational assignment and has identified characteristic vibrational signatures associated with particular conformational families-including those that do or do not display inter-ring hydrogen bonding across the glycosidic linkage. In addition, the IR spectra of the monosaccharide moieties provide benchmarks, through which the conformational assignments can be refined. This introduces a general concept of modularity and secondary structure in oligosaccharides-essential for the success of similar studies on larger oligosaccharides in the future.
• A<i>C</i>-linked Glycomimetic in the Gas Phase and in Solution: Synthesis and Conformation of the Disaccharide Manα(1,6)-<i>C</i>-ManαOPh
  作者：Ludovic Drouin、E. Cristina Stanca-Kaposta、Priptal Saundh、Antony J. Fairbanks、Sebastian Kemper、Timothy D. W. Claridge、John P. Simons

  DOI：10.1002/chem.200802179

  日期：2009.4.14

  The effect of carbon is subtle but sweet: The flexible C‐linkage in the newly synthesised C‐glycosyl mimetic, Manα(1,6)‐C‐ManαOPh allows OHπ bonding, both in the gas phase and in aqueous solution. This interaction is absent in the O‐linked disaccharide (see figure).

  碳的效果是微妙的，但甜：在新合成的柔性C-联动Ç α-糖基模拟物，Manα（1,6） - c ^ -ManαOPh允许OH  π键合，无论是在气相中和在水溶液中。O联二糖中不存在这种相互作用（见图）。