(2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-phenyltetrahydro-2H-pyran-3-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-phenyltetrahydro-2H-pyran-3-ol
• 英文别名: (2R,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-tetrahydro-pyran-3-ol；phenyl 1-(3,4,6-tri-O-benzyl-1-deoxy-α-D-glucopyranosyl)；(2R,3S,4R,5R,6R)-2-phenyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• 化学式: C₃₃H₃₄O₅
• 分子量: 510.63
• InChiKey: YJTGPJSHMXGKDE-CVCQUZQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4,6-三苄氧基-D-葡萄烯糖 在 二甲基二环氧乙烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 (2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-phenyltetrahydro-2H-pyran-3-ol
  参考文献：
  名称：

  Zinc-Mediated Synthesis of α-C-Glycosides from 1,2-Anhydroglycosides

  摘要：

  α-C-糖苷是通过将有机锌试剂加入糖醇环氧化物制备的。在CF3COOH的存在下，二烷基和二芳基锌试剂能以53-82%的产率提供相应的α-糖苷。由RLi与氯化锌反应形成的有机锌氯化物RZnCl也可以成功应用于这种偶联反应，并具有很高的α-选择性。

  DOI：

  10.1055/s-2003-38751

文献信息

• Light-Mediated Cross-Coupling of Anomeric Trifluoroborates
  作者：Eric M. Miller、Maciej A. Walczak

  DOI：10.1021/acs.orglett.1c01035

  日期：2021.6.4

  Stereoselective reactions at the anomeric carbon constitute the cornerstone of preparative carbohydrate chemistry. Here, we report stereoselective C-arylation and etherification reactions of anomeric trifluoroborates derived from BMIDA esters. These reactions are characterized by high anomeric selectivities for 2-deoxysugars and broad substrate scope (24 examples), including disaccharides and trifluoroborates

  异头碳的立体选择性反应构成制备碳水化合物化学的基石。在这里，我们报告了衍生自 BMIDA 酯的异头三氟硼酸盐的立体选择性 C-芳基化和醚化反应。这些反应的特点是对 2-脱氧糖具有高异头选择性和广泛的底物范围（24 个例子），包括具有游离羟基的二糖和三氟硼酸盐。总之，这种新型碳水化合物试剂增加了适用于有效安装 C-C 键的异头亲核试剂的调色板。
• Highly Stereospecific Cross-Coupling Reactions of Anomeric Stannanes for the Synthesis of C-Aryl Glycosides
  作者：Feng Zhu、Michael J. Rourke、Tianyi Yang、Jacob Rodriguez、Maciej A. Walczak

  DOI：10.1021/jacs.6b07891

  日期：2016.9.21

  We demonstrate that configurationally stable anomeric stannanes undergo a stereospecific cross-coupling reaction with aromatic halides in the presence of a palladium catalyst with exceptionally high levels of stereocontrol. In addition to a broad substrate scope (>40 examples), this reaction eliminates critical problems inherent to nucleophilic displacement methods and is applicable to (hetero)aromatics

  我们证明，在具有极高立体控制水平的钯催化剂存在下，构型稳定的异头锡烷与芳族卤化物发生立体定向交叉偶联反应。除了广泛的底物范围（> 40 个例子）之外，该反应消除了亲核置换方法固有的关键问题，适用于（杂）芳烃、肽、药物、常见单糖和含有游离羟基的糖类。
• Cytotoxic effects of C-glycosides in HOS and HeLa cell lines
  作者：Carlos A. Sanhueza、Carlos Mayato、Rubén P. Machı´n、José M. Padrón、Rosa L. Dorta、Jesús T. Vázquez

  DOI：10.1016/j.bmcl.2007.04.060

  日期：2007.7

  Fifty-two C-glycosides were synthesized and their in-vitro antiproliferative activity screened against human cervical carcinoma (HeLa) and osteosarcoma (HOS) cell lines. Nine of them had growth inhibitions (GI(50) values) below 10 mu M, the Gglucopyranoside 38 being the most active against HeLa (5.4 mu M) and the dichlorocyclopropyl derivative 42 against HOS (1.6 mu M). Some preliminary structure-activity relationships were established. (c) 2007 Elsevier Ltd. All rights reserved.
• C-Glycosides to fused polycyclic ethers
  作者：Shawn P. Allwein、Jason M. Cox、Brett E. Howard、Henry W.B. Johnson、Jon D. Rainier

  DOI：10.1016/s0040-4020(02)00057-1

  日期：2002.3

  This manuscript describes the synthesis of fused polycyclic ethers from the coupling of C-glycoside forming reactions with ring closing metathesis and acid mediated annulation reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Aluminum- and Boron-Mediated C-Glycoside Synthesis from 1,2-Anhydroglycosides
  作者：Jon D. Rainier、Jason M. Cox

  DOI：10.1021/ol006286u

  日期：2000.8.1

  [GRAPHICS]This letter describes a single flask strategy to the synthesis of a alpha-C-glycosides from glycals. This protocol couples a glycal epoxidation reaction with a C-2 alkoxy-directed carbon-carbon bond forming reaction.