(2S,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-phenyltetrahydro-2H-pyran-3-ol | 130912-38-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-phenyltetrahydro-2H-pyran-3-ol
• 英文别名: (2S,3S,4R,5R,6R)-2-phenyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 130912-38-8
• 化学式: C₃₃H₃₄O₅
• 分子量: 510.63
• InChiKey: YJTGPJSHMXGKDE-MRRLEEDCSA-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：

  (3R,4R,5S)-4,5-Bis-benzyloxy-3-benzyloxymethyl-2,7-dioxa-bicyclo[4.1.0]heptane 在 potassium fluoride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 C₅₁H₇₃O₂P 、 copper(l) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 74.0h， 生成 (2S,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-phenyltetrahydro-2H-pyran-3-ol
  参考文献：
  名称：

  用于合成 C-芳基糖苷的异头锡烷的高度立体特异性交叉偶联反应

  摘要：

  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。

  DOI：

  10.1021/jacs.6b07891

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。
• Formation of C-glycosides by a palladium-catalysed coupling reaction of tributylstannyl glycals with organic halides
  作者：Eric Dubois、Jean-Marie Beau

  DOI：10.1039/c39900001191

  日期：——

  The palladium-catalysed coupling reaction of 1-(tributylstannyl)-D-glucals with unsaturated halides furnishes the corresponding 1-C-alkylated glucals, an efficient procedure for a symmetric or dis-symmetric di-C-glycosidation of 1,3-dibromobenzene.

  1-（三丁基锡烷基）-D-葡糖与不饱和卤化物的钯催化偶联反应提供了相应的1- C-烷基化的葡糖，这是1,3-二溴苯对称或不对称二C-糖基化的有效方法。
• Synthesis of C-glycopyranosyl compounds by a palladium-catalyzed coupling reaction of 1-tributylstannyl-d-glucals with organic halides
  作者：Eric Dubois、Jean-Marie Beau

  DOI：10.1016/s0008-6215(00)90552-4

  日期：1992.4

  1-Tributylstannyl-D-glucals, prepared from the corresponding 1-phenylsulfonyl-D-glucals, were coupled efficiently to various organic halides in the presence of a palladium(0) catalyst. This mild reaction is specially useful for the preparation of 1-C-aryl-D-glucals and compatible with unprotected hydroxy groups or hindered aromatic bromides. It has been shown that the resulting 1-C-aryl(alkyl)-D-glucals

  由相应的1-苯基磺酰基-D-葡萄糖制备的1-三丁基锡烷基-D-葡萄糖在钯（0）催化剂的存在下有效地偶联到各种有机卤化物上。这种温和的反应对于制备1-C-芳基-D-葡萄糖特别有用，并且与未保护的羟基或受阻的芳香族溴化物相容。已经表明，所得的1-C-芳基（烷基）-D-葡萄糖适用于烯醇醚基团的进一步合成操作，包括立体选择性氢化，硼氢化-氧化或环氧化。所有形成的化合物都是由试剂对葡糖衍生物的α-面的攻击所致。反应扩展到1，3-，1，4-二-和1,3,5-三溴苯，导致相应的对称的二-（三）-C-葡萄糖基苯。最后，顺序的二-C-葡萄糖基化为1
• Development of Routes for the Stereoselective Preparation of β-Aryl-<i>C</i>-glycosides via <i>C</i>-1 Aryl Enones
  作者：Adesh Kumar Singh、Vimlesh Kumar Kanaujiya、Varsha Tiwari、Shahulhameed Sabiah、Jeyakumar Kandasamy

  DOI：10.1021/acs.orglett.0c02843

  日期：2020.10.2

  various arylboronic acids bearing electron-donating and -withdrawing groups in the presence of palladium acetate and 1,10-phenanthroline. These reactions provided synthetically useful C-1 aryl enones in good yields. Many sensitive functional groups as well as protecting groups present in arylboronic acids and enones, respectively, remained intact under optimized conditions. The stereoselective hydrogenation

  宽范围的烯酮衍生自d -glucal，d -galactal，升-rhamnal，d -rhamnal，和升-arabinal后行与各种芳基硼酸轴承供电子和在乙酸钯的存在吸电子基团的Heck耦合和1,10-菲咯啉。这些反应以良好的产率提供了合成上有用的C -1芳基烯酮。在优化的条件下，芳基硼酸和烯酮中分别存在的许多敏感官能团和保护基团保持完整。C -1芳基烯酮与Pd-C / H 2的立体选择性加氢提供2-脱氧芳基-C的β-异构体-糖苷具有优异的产率。所述C- 1芳基烯酮也被用来作为用于2-羟基β -芳基-的合成前体Ç -glycosides。以优异的产率实现了C -1芳基烯酮的区域选择性C -2卤化和乙烯基化。
• 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.