2-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-3,4,5-trimethoxyphen-1-ol | 350480-15-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-3,4,5-trimethoxyphen-1-ol
• 英文别名: 2-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-3,4,5-trimethoxyphenol；3,4,5-trimethoxy-2-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]phenol
• CAS: 350480-15-8
• 化学式: C₄₃H₄₆O₉
• 分子量: 706.833
• InChiKey: QNOWWJJJFYPUDQ-FBCYNMMMSA-N

物化性质

• 沸点：
  768.5±60.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  52
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  94.1
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-3,4,5-trimethoxyphen-1-ol 在 palladium diacetate 4-二甲氨基吡啶 、 1,1'-双(二苯基膦)二茂铁 、 氯化亚砜 、 palladium hydroxide - carbon 、 lutidine 、 1,3-双(二苯基膦)丙烷 、 氢气 、 potassium acetate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 25.0h， 生成 二-O-甲基岩白菜素
  参考文献：
  名称：

  Short Total Synthesis of 8,10-Di-O-methylbergenin

  摘要：

  A short, high-yielding synthesis of the C-glucoside 8,10-di-O-methylbergenin is reported. Key elements of the synthesis are a stereoselective installation of a beta-C-aryl linkage, a palladium(0)-catalyzed aryl carbonylation, and a regioselective lactonization reaction. This pathway should allow access to a host of bergenin analogues.

  DOI：

  10.1021/ol026378e
• 作为产物：
  描述：

  3,4,5-三甲氧基苯酚 、 2,3,4,6-tetra-O-benzyl-D-glucopyranose trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以67%的产率得到2-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-3,4,5-trimethoxyphen-1-ol
  参考文献：
  名称：

  Short Total Synthesis of 8,10-Di-O-methylbergenin

  摘要：

  A short, high-yielding synthesis of the C-glucoside 8,10-di-O-methylbergenin is reported. Key elements of the synthesis are a stereoselective installation of a beta-C-aryl linkage, a palladium(0)-catalyzed aryl carbonylation, and a regioselective lactonization reaction. This pathway should allow access to a host of bergenin analogues.

  DOI：

  10.1021/ol026378e

文献信息

• Oligosaccharide Synthesis with Glycosyl Phosphate and Dithiophosphate Triesters as Glycosylating Agents
  作者：Obadiah J. Plante、Emma R. Palmacci、Rodrigo B. Andrade、Peter H. Seeberger

  DOI：10.1021/ja016227r

  日期：2001.10.1

  Described is an efficient one-pot synthesis of alpha- and beta-glycosyl phosphate and dithiophosphate triesters from glycals via 1,2-anhydrosugars. Glycosyl phosphates function as versatile glycosylating agents for the synthesis of beta-glucosidic, beta-galactosidic, alpha-fucosidic, alpha-mannosidic, beta-glucuronic acid, and beta-glucosamine linkages upon activation with trimethylsilyl trifluoromethanesulfonate

  描述了通过 1,2-脱水糖从糖基中高效地一锅合成α-和β-糖基磷酸酯和二硫代磷酸三酯。糖基磷酸酯用作多功能糖基化剂，用于合成 β-葡糖苷、β-半乳糖苷、α-岩藻糖苷、α-甘露糖苷、β-葡糖醛酸和 β-葡糖胺键，在用三甲基甲硅烷基三氟甲磺酸酯 (TMSOTf) 活化后。除了作为 O-糖基化的有效供体，糖基磷酸酯还可有效制备 S-糖苷和 C-糖苷。此外，还讨论了糖基磷酸酯与甲硅烷基化受体的酸催化偶联。糖基二硫代磷酸酯被合成并且也用作糖基供体。这种替代方法提供了与含有糖基的受体的兼容性，以形成 β-糖苷。为了最大限度地减少保护基团的操作，报告了使用糖基磷酸酯的正交和区域选择性糖基化策略。描述了一种正交糖基化方法，包括在硫糖苷受体存在下激活磷酸糖基供体，以及受体介导的区域选择性糖基化策略。此外，公开了利用α-和β-糖基磷酸酯反应性差异的独特糖基化策略。此处概述的程序为在溶液中组装复杂寡糖以及通过单
• Synthesis of <i>C</i>-Aryl and <i>C</i>-Alkyl Glycosides Using Glycosyl Phosphates
  作者：Emma R. Palmacci、Peter H. Seeberger

  DOI：10.1021/ol0158462

  日期：2001.5.1

  [reaction: see text] Mannosyl and glucosyl phosphate donors were successfully used in constructing C-aryl linkages common to many natural products via a Lewis acid induced Fries-like rearrangement. The rearrangement was stereo- and regiospecific, yielding only one C-glycoside product. C-Alkyl glycoside carbohydrate mimetics were generated by using silicon-derived C-nucleophiles and glycosyl phosphates

  [反应：见正文]甘露糖基和葡萄糖基磷酸供体已成功用于通过路易斯酸诱导的弗里斯样重排构建许多天然产物共有的C-芳基键。重排是立体和区域特异性的，仅产生一种C-糖苷产物。通过使用硅衍生的C-亲核试剂和糖基磷酸酯生成C-烷基糖苷碳水化合物模拟物。
• Aryl C-glycosylation using an ionic liquid containing a protic acid
  作者：Chigusa Yamada、Kaname Sasaki、Shuichi Matsumura、Kazunobu Toshima

  DOI：10.1016/j.tetlet.2007.04.077

  日期：2007.6

  Aryl C-glycosylation of several glycosyl donors, including unprotected sugars, with phenol and naphthol derivatives in an ionic liquid containing a protic acid proceeded effectively and stereoselectively to give the corresponding aryl C-glycosides in good to high yields. Because the ionic liquid was nonvolatile, the reaction could be carried out under reduced pressure; in addition, the ionic liquid could be reused without loss of effectiveness. These features contribute to the significant advantages of this novel aryl C-glycosylation reaction. (c) 2007 Elsevier Ltd. All rights reserved.
• Short Total Synthesis of 8,10-Di-<i>O</i>-methylbergenin
  作者：Holger Herzner、Emma R. Palmacci、Peter H. Seeberger

  DOI：10.1021/ol026378e

  日期：2002.8.1

  A short, high-yielding synthesis of the C-glucoside 8,10-di-O-methylbergenin is reported. Key elements of the synthesis are a stereoselective installation of a beta-C-aryl linkage, a palladium(0)-catalyzed aryl carbonylation, and a regioselective lactonization reaction. This pathway should allow access to a host of bergenin analogues.