tert-butyl 2,3,4,6-tetra-O-benzyl-α,β-D-glucopyranoside | 367946-92-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl 2,3,4,6-tetra-O-benzyl-α,β-D-glucopyranoside
• 英文别名: (3R,4S,5R,6R)-2-[(2-methylpropan-2-yl)oxy]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 367946-92-7
• 化学式: C₃₈H₄₄O₆
• 分子量: 596.764
• InChiKey: XDIPNAGULDXWAU-YGMGGQQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-oxopropyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 在 4 A molecular sieve 、 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 tert-butyl 2,3,4,6-tetra-O-benzyl-α,β-D-glucopyranoside
  参考文献：
  名称：

  Design, Development and Utility of Glycosyl Donors Bearing an Acetoxymethoxy Leaving Group

  摘要：

  已制备新型糖苷供体 2d、4d 和 6d，具有“乙酰氧基-甲氧基”离去基团，并通过将其与醇 A-G 结合，利用 BF3-Et2O 作为促使剂，展示了它们的实用性，从而获得了二糖和三糖。

  DOI：

  10.1246/cl.1998.863

文献信息

• A New, Efficient Glycosylation Method for Oligosaccharide Synthesis under Neutral Conditions:  Preparation and Use of New DISAL Donors
  作者：Lars Petersen、Knud J. Jensen

  DOI：10.1021/jo0057654

  日期：2001.9.1

  Efficient, stereoselective glycosylation methods are required for the synthesis of complex oligosaccharides as tools in glycobiology. All glycosylation methods, which have found wide acceptance, rely on Lewis acid activation of glycosyl donors prior to glycosylation. Here, we present a new and efficient method for glycosylation under neutral or mildly basic conditions. Glycosides of methyl 2-hydroxy-3

  需要高效，立体选择性的糖基化方法来合成复杂的寡糖，并将其作为糖生物学的工具。已经被广泛接受的所有糖基化方法都依赖于糖基化之前糖基供体的路易斯酸活化。在这里，我们提出了一种在中性或轻度碱性条件下糖基化的新方法。通过亲核芳族取代制备2-羟基-3,5-二硝基苯甲酸甲酯（DISAL）及其对位异构体4-羟基-3,5-二硝基苯甲酸甲酯的糖苷。在它们作为糖基供体的潜力的第一个证明中，实现了甲醇的立体定向糖基化。在受阻醇的糖基化反应中，β-给体被证明具有更高的反应性，并且主要形成了α-葡萄糖苷。被保护的单糖的糖基化，在没有路易斯酸和碱的情况下，在40-60℃下于1-甲基-2-吡咯烷酮（NMP）中平稳地进行与游离的6-OH或3-OH的反应，获得了良好的产率。3-OH的糖基化仅产生α-连接的二糖。
• Generation of Alkoxycarbenium Ion Pools from Thioacetals and Applications to Glycosylation Chemistry
  作者：Shinkiti Suzuki、Kouichi Matsumoto、Kohsuke Kawamura、Seiji Suga、Jun-ichi Yoshida

  DOI：10.1021/ol048524h

  日期：2004.10.1

  [reaction: see text] Alkoxycarbenium ions have been generated and accumulated as "cation pools" by the low-temperature electrochemical oxidation of alpha-phenylthioethers. Although an unsuccessful attempt to accumulate glycosyl cations was made, a one-pot method for electrochemical glycosylation, which involves anodic oxidation of thioglycosides to generate glycosyl cation equivalents followed by their reactions

  [反应：见正文]通过α-苯基硫醚的低温电化学氧化，已生成烷氧基碳鎓离子并将其积累为“阳离子池”。尽管进行了积累糖基阳离子的尝试，但未成功，但已经开发出了一种一锅法的电化学糖基化方法，该方法涉及将硫糖苷进行阳极氧化以生成糖基阳离子等价物，然后使其与糖基受体反应。
• Catalytic and stereoselective glycosylation with glycosyl N-trichloroacetylcarbamate
  作者：Jun-ichi Matsuo、Tatsuya Shirahata、Satoshi Ōmura

  DOI：10.1016/j.tetlet.2005.11.027

  日期：2006.1

  Catalytic and stereoselective glycosylation efficiently proceeded by activating a glycosyl N-trichloroacetylcarbamate with a catalytic amount of Lewis acids in the presence of a glycosyl acceptor and molecular sieves 5 angstrom. Catalytic and one-pot dehydrative glycosylation of a 1-hydroxy carbohydrate was also performed stereoselectively by the reaction with trichloroacetyl isocyanate followed by activation with a catalytic amount of activators. (c) 2005 Elsevier Ltd. All rights reserved.
• Glycosyl trichloroacetylcarbamate: a new glycosyl donor for O-glycosylation
  作者：K. Jayakanthan、Yashwant D. Vankar

  DOI：10.1016/j.carres.2005.07.024

  日期：2005.12

  Glycosyl trichloroacetylcarbamates, readily obtained by reacting 1-hydroxy sugars with trichloroacetylisocyanate, have been found as excellent glycosyl donors, and the corresponding O-glycosides are formed in good to excellent yields with a fairly good degree of selectivity. (c) 2005 Elsevier Ltd. All rights reserved.
• Electrochemical glycosylation method
  作者：Ryoji Noyori、Isao Kurimoto

  DOI：10.1021/jo00372a050

  日期：1986.10