(2R,3R,4S,5R,6S)-2-((((2S,4R,5S,6R)-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl tribenzoate | 1063596-40-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6S)-2-((((2S,4R,5S,6R)-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl tribenzoate
• CAS: 1063596-40-6
• 化学式: C₄₀H₄₂O₁₆
• 分子量: 778.764
• InChiKey: AEWGPJWZYDYAEQ-FLFUWWHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  56.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  194.72
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzoyl-6-O-(2-S-acetyl-3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-α-D-glucopyranoside 在 一水合肼 、 tris(2,2'-bipyridyl)ruthenium dichloride 、 三(2-羰基乙基)磷盐酸盐 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以84 %的产率得到(2R,3R,4S,5R,6S)-2-((((2S,4R,5S,6R)-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl tribenzoate
  参考文献：
  名称：

  Visible-Light-Promoted Desulfurization to Synthesize Deoxyglycosides

  摘要：

  DOI：

  10.1021/acs.joc.3c00046

文献信息

• Gold(I)-Catalyzed Glycosylation with Glycosyl<i>ortho</i>-Alkynylbenzoates as Donors: General Scope and Application in the Synthesis of a Cyclic Triterpene Saponin
  作者：Yao Li、Xiaoyu Yang、Yunpeng Liu、Cunsheng Zhu、You Yang、Biao Yu

  DOI：10.1002/chem.200902548

  日期：2010.2.8

  coupling with the poorly nucleophilic amides gives satisfactory yields. Moreover, excellent α‐selective glycosylation with a 2‐deoxy sugar donor and β‐selective sialylation have been realized. Application of the present glycosylation protocol in the efficient synthesis of a cyclic triterpene tetrasaccharide have further demonstrated the versatility and efficacy of this new method, in that a novel chemoselective

  糖基邻炔基苯甲酸酯已成为在金（I）配合物如Ph 3 PAuOTf和Ph 3 PAuNTf 2催化下进行糖苷化的新一代供体（Tf ＝三氟甲磺酸盐）。这些供体种类繁多，包括2-脱氧糖和唾液酸供体，易于制备且易于保存。与醇类的糖苷偶联收率通常非常好；即使与不良亲核酰胺直接偶联也能获得令人满意的收率。此外，已经实现了具有2-脱氧糖供体的出色的α-选择性糖基化和β-选择性唾液酸化。本糖基化方案在环状三萜四糖高效合成中的应用进一步证明了这种新方法的多功能性和有效性，因为已实现了羧酸的新型化学选择性糖基化和新的单锅顺序糖基化序列。
• Characterization of the Isochromen-4-yl-gold(I) Intermediate in the Gold(I)-Catalyzed Glycosidation of Glycosyl ortho-Alkynylbenzoates and Enhancement of the Catalytic Efficiency Thereof
  作者：Yugen Zhu、Biao Yu

  DOI：10.1002/anie.201103409

  日期：2011.8.29

  Gold standard: The title gold complex (see scheme) was characterized unambiguously as an important intermediate in the title reaction. Protonolysis of this vinyl gold(I) complex was critical for regeneration of the active gold(I) species for the catalytic cycle, and use of a protic acid co‐catalyst significantly lowered the required catalyst loading to 0.5 mol %.

  金标准：标题金络合物（参见方案）被明确表征为标题反应中的重要中间体。该乙烯基金（I）配合物的质子分解对于活性金（I）物种在催化循环中的再生至关重要，并且使用质子酸助催化剂可将所需的催化剂负载量大大降低至0.5 mol％。
• Direct and Stereoselective Synthesis of α-Linked 2-Deoxyglycosides
  作者：Jin Park、Thomas J. Boltje、Geert-Jan Boons

  DOI：10.1021/ol801833n

  日期：2008.10.2

  alpha-Linked 2-deoxyglycosides were conveniently obtained by employing a glycosyl donor having a participating ( S)-(phenylthiomethyl)benzyl moiety at C-6, whereas 2,6-dideoxy-alpha-glycosides could be prepared by BF 3.Et 2O-promoted activation of allyl glycosyl donors.

  α-连接的 2-脱氧糖苷可以通过使用在 C-6 处具有参与 (S)-(苯硫基甲基) 苄基部分的糖基供体方便地获得，而 2,6-双脱氧-α-糖苷可以通过 BF 3.Et 2O 制备- 促进烯丙基糖基供体的活化。
• GeCl₂·Dioxane–AgBF₄ Catalyzed Activation of Glycosyl Fluorides for Glycosylation
  作者：Qiuyu Zhu、Yu Tang、Biao Yu

  DOI：10.1021/acs.orglett.2c01146

  日期：2022.5.27

  catalytic glycosyl fluoride activation system using the GeCl2·dioxane–AgBF4 combination was developed, which involves a reversible activation of the anomeric C–F bond by a [Ge(II)–Cl]+ cation and a reversible chloride ion transfer between Ge(II) and glycosyl cations. This catalytic glycosylation system is easy to operate, proceeds at room temperature, and offers a broad scope of substrates.

  开发了一种使用 GeCl 2 ·二恶烷-AgBF 4组合的催化糖基氟化物活化系统，该系统涉及通过 [Ge(II)-Cl] +阳离子对异头 C-F 键的可逆活化和在它们之间的可逆氯离子转移。 Ge(II) 和糖基阳离子。这种催化糖基化系统易于操作，在室温下进行，并提供广泛的底物。
• Gold-Catalyzed Synthesis of 2-Deoxy Glycosides Using <i>S</i>-But-3-ynyl Thioglycoside Donors
  作者：Surya Adhikari、Kedar N. Baryal、Danyang Zhu、Xiaohua Li、Jianglong Zhu

  DOI：10.1021/cs300670k

  日期：2013.1.4

  A mild and atom-economic gold(I)-catalyzed glycosylation for stereoselective synthesis of 2-deoxy alpha-glycosides using bench-stable 2-deoxy S-But-3-ynyl thioglycoside donors has been described. Under optimal conditions, 2-deoxy and 2,6-dideoxy thioglycoside donors were able to react with a variety of primary, secondary, and tertiary alcohol acceptors to afford alpha-selective glycosides in good to excellent yields.