1-O-benzoyl-α-D-glucopyranose | 123632-51-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-benzoyl-α-D-glucopyranose
• 英文别名: 1-o-Benzoyl alpha-d-glucopyranoside；[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] benzoate
• CAS: 123632-51-9
• 化学式: C₁₃H₁₆O₇
• 分子量: 284.266
• InChiKey: LVFCLUMIBMHAFL-BZNQNGANSA-N

物化性质

• 沸点：
  507.1±50.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl β-D-glucopyranoside 在 三氟化硼乙醚 、 sodium 2,2,2-trifluoroacetate 、 碳酸氢钠 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 3.25h， 生成 1-O-benzoyl-α-D-glucopyranose
  参考文献：
  名称：

  2-(Trimethylsilyl)ethyl glycosides. 3. Synthesis, anomeric deblocking, and transformation into 1,2-trans 1-O-acyl sugars

  摘要：

  DOI：

  10.1021/jo00259a006

文献信息

• One-Step Stereocontrolled Synthesis of α-Anomeric Carboxylic Acid Esters from Unprotected Glycosyl Donors: A Water-Soluble Aspirin Pro-Drug Analogue­
  作者：Stephen Hanessian、Vincent Mascitti、Pu-Ping Lu、Hideki Ishida

  DOI：10.1055/s-2002-34372

  日期：——

  The reaction of 2-(3-methoxypyridyl) β-d-gluco- and d-galactopyranosides with various carboxylic acids affords the corresponding α-1-esters in high yields. Aspirin can be solubilized in water as the α-d-galactopyranosyl ester.

  2-(3-甲氧基吡啶基)的β-D-葡萄糖苷和D-半乳糖苷与多种羧酸反应，以高产率生成相应的α-1-酯。阿司匹林可以作为α-D-半乳糖苷酯在水中的可溶形式存在。
• Anomeric alkylations and acylations of unprotected mono- and disaccharides mediated by pyridoneimine in aqueous solutions
  作者：Kalyan Dey、Narayanaswamy Jayaraman

  DOI：10.1039/d1cc07056h

  日期：——

  A site-specific deprotonation followed by alkylations and acylations of sugar hemiacetals to the corresponding alkyl glycosides and acylated sugars in aqueous solutions is disclosed herein. Pyridoneimine as a new base is developed to mediate the deprotonation of readily available sugar hemiacetals and further reactions with alkylation and acylation agents.

  本文公开了在水溶液中进行位点特异性去质子化，随后将糖半缩醛烷基化和酰化为相应的烷基糖苷和酰化糖。吡啶酮亚胺作为一种新的碱被开发用于介导容易获得的糖半缩醛的去质子化以及与烷基化和酰化剂的进一步反应。
• Stereoselective synthesis of β-glycosyl esters of cis-cinnamic acid and its derivatives using unprotected glycosyl donors
  作者：Kazumasa Matsuo、Keisuke Nishikawa、Mitsuru Shindo

  DOI：10.1016/j.tetlet.2011.08.104

  日期：2011.10

  The β-glycosyl esters of cis-cinnamic acid were synthesized directly using Hannesian’s unprotected glycosyl donor and the carboxylic acid in toluene. This protocol does not require protecting groups on the glycosyl donors, and high stereoselectivity was achieved. The first synthesis of a potent allelochemical, 1-O-cis-cinnamoyl-β-d-glucopyranose, is also described.

  使用Hannesian未保护的糖基供体和甲苯中的羧酸，直接合成了顺式肉桂酸的β-糖基酯。该方案不需要糖基供体上的保护基，并且实现了高立体选择性。还描述了有效的化感化学物质1 - O-顺式-肉桂酰基-β-d-吡喃葡萄糖的首次合成。
• Solvent-Dependent Mechanism and Stereochemistry of Mitsunobu Glycosylation with Unprotected Pyranoses
  作者：Hironori Takeuchi、Yusuke Fujimori、Yoshihiro Ueda、Hiromitsu Shibayama、Masaru Nagaishi、Tomoyuki Yoshimura、Takahiro Sasamori、Norihiro Tokitoh、Takumi Furuta、Takeo Kawabata

  DOI：10.1021/acs.orglett.0c01549

  日期：2020.6.19

  acidic glycosyl acceptors such as carboxylic acids, phenols, and imides, retaining its high stereoselectivity (33 examples). Glycosylation of a carboxylic acid with unprotected α-d-mannose proceeded also in an SN2 manner to directly afford a usually less accessible 1,2-cis-mannoside. One- or two-step total syntheses of five simple natural glycosides were performed using the glycosylation strategy presented

  在Mitsunobu条件下，在二恶烷中，用未保护的α- d-葡萄糖对苯甲酸高度立体选择性糖基化提出了一种S N 2机制，而在DMF中，对于非立体选择性糖基化则提出了一种S N 1机制。S N 2型立体选择性Mitsunobu糖基化通常可作为糖基供体与多种酸性糖基受体（如羧酸，酚和酰亚胺）结合使用，作为糖基供体，适用于各种未保护的吡喃糖，保持其高立体选择性（33个例子）。羧酸与未保护的α- d-甘露糖的糖基化也以S N 2方式进行，以直接提供通常较难获得的1,2-顺式-甘露糖苷。使用未保护的α- d-葡萄糖，使用此处介绍的糖基化策略进行五个简单天然糖苷的一步或两步总合成。
• Base‐Promoted Glycosylation Allows Protecting Group‐Free and Stereoselective <i>O</i>‐Glycosylation of Carboxylic Acids**
  作者：Hao Zuo、Chen Zhang、Yang Zhang、Dawen Niu

  DOI：10.1002/anie.202309887

  日期：2023.10.16

  Here we report a simple and general method to achieve fully unprotected, stereoselective glycosylation of carboxylic acids, employing bench‐stable allyl glycosyl sulfones as donors. Running the glycosylation reaction under basic conditions was crucial for the efficiencies and selectivities. Both the donor activation stage and the glycosidic bond forming stage of the process are compatible with free hydroxyl groups, thereby allowing for the use of fully unprotected glycosyl donors. This transformation is stereoconvergent, occurs under mild and metal‐free conditions at ambient temperature with visible light (455 nm) irradiation, and displays remarkable scope with respect to both reaction partners. Many natural products and commercial drugs, including an acid derived from the complex anticancer agent taxol, were efficiently glycosylated. Experimental studies provide insights into the origin of the stereochemical outcome.

  摘要我们在此报告了一种简单而通用的方法，该方法采用台式稳定的烯丙基糖基砜作为给体，实现了羧酸的完全无保护、立体选择性糖基化。在碱性条件下进行糖基化反应对效率和选择性至关重要。该过程的供体活化阶段和糖苷键形成阶段都与游离羟基兼容，因此可以使用完全无保护的糖基供体。这种转化具有立体转换性，在环境温度和可见光（455 纳米）照射下，在温和、无金属的条件下进行，而且对两个反应伙伴都有显著的影响。许多天然产物和商业药物，包括从复合抗癌剂紫杉醇中提取的一种酸，都被有效地糖基化了。实验研究为了解立体化学结果的起源提供了见解。