allyl 3-O-benzyl-D-glucopyranoside | 209911-52-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3-O-benzyl-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R)-2-(hydroxymethyl)-4-phenylmethoxy-6-prop-2-enoxyoxane-3,5-diol
• CAS: 209911-52-4
• 化学式: C₁₆H₂₂O₆
• 分子量: 310.347
• InChiKey: RWGJIOGFEPTYIA-YFVFXCHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl 3-O-benzyl-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydride 作用下， 反应 32.0h， 生成 allyl-2,3,4-tri-O-benzyl-6-O-trityl-D-glucopyranoside
  参考文献：
  名称：

  从D-葡萄糖到D-肌醇-1，4，5-（三磷酸二氢）的合成路线：使用不寻常的烯反应和Bu 2 SnCl 2 / Bu 2 SnH 2试剂

  摘要：

  d-葡萄糖转化为炔丙基硅烷醛3，在樟脑磺酸存在下进行闭环并保留硅，得到5，然后通过酮22精制为2，之前已转化为d -肌醇-1，4，5-三（磷酸二氢）。合成中的关键步骤是用Bu 2 SnCl 2 / Bu 2 SnH 2选择性立体还原22，该试剂系统对生成赤道醇表现出强烈的偏好。

  DOI：

  10.1016/s0040-4039(98)00792-8
• 作为产物：
  描述：

  在 氨 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以85%的产率得到allyl 3-O-benzyl-D-glucopyranoside
  参考文献：
  名称：

  GlcNAc（β1→4）Glc二糖的强杀菌作用：合成，生理效应和几丁质酶抑制。

  摘要：

  含有2- O-乙酰基和/或6-硫酸根基团的四种GlcNAc（β1→4）Glc二糖的合成产率高，总1,2-反式立体选择性。这些二糖被评估为昆虫几丁质酶抑制和杀蚜活性的候选者。所制备的所有化合物对桃蚜的蚜虫均显示出生理作用。但是，根据微妙的结构特征，不同来源（细菌，真菌和蚜虫）的几丁质酶的抑制作用遵循不同的模式。

  DOI：

  10.1002/chem.201200887

文献信息

• Synthetic Study on Lipoteichoic Acid of Gram Positive Bacteria. I. Synthesis of Proposed Fundamental Structure of<i>Streptococcus pyogenes</i>Lipoteichoic Acid
  作者：Koichi Fukase、Takahiro Matsumoto、Naoko Ito、Takuya Yoshimura、Shozo Kotani、Shoichi Kusumoto

  DOI：10.1246/bcsj.65.2643

  日期：1992.10

  Synthetic study on Streptococcus pyogenes lipoteichoic acid (LTA) which was reported to induce nontoxic TNF is described. The proposed fundamental structure of LTA was constructed by coupling of the glycolipid part with the poly(glycerol phosphate) (PGP) part and subsequent deprotection. The PGP part was prepared by a simple repeating procedure using the phosphoramidite method for the construction

  描述了对据报道可诱导无毒 TNF 的化脓性链球菌脂磷壁酸 (LTA) 的合成研究。LTA 的基本结构是通过将糖脂部分与聚（甘油磷酸）（PGP）部分偶联并随后去保护来构建的。PGP 部分是通过简单的重复程序制备的，使用亚磷酰胺方法构建 1,3-磷酸二酯键。糖脂部分是使用适当的糖基氟作为供体合成的，其中对硝基苄基成功地用于临时保护羟基官能团。
• Formal Synthesis of <scp>d</scp>-<i>myo</i>-Inositol 1,4,5-Tris(dihydrogen phosphate):  Cyclization by an Unusual Ene Reaction and Use of the Bu₂SnCl₂/Bu₂SnH₂ Reagent for Generating an Equatorial Alcohol
  作者：Derrick L. J. Clive、Xiao He、Maarten H. D. Postema、M. Jeffrey Mashimbye

  DOI：10.1021/jo990086i

  日期：1999.6.1

  D-Glucose was converted into the propargyl silane aldehyde 5, which, on treatment with camphorsulfonic acid, cyclized with retention of silicon. The allenic product (7) was elaborated via ketone 24 into 4, which had previously been converted into D-myo-inositol 1,4,5-tris(dihydrogen phosphate). Selective reduction of the advanced intermediate 24 was accomplished with Bu2SnCl2/Bu2SnH2, a reagent mixture that shows a very strong preference for generating equatorial alcohols. The cyclization step leading to allene 7 was studied by examining a number of model compounds; the unusual retention of silicon appears to be limited to highly oxygenated substrates, such as 5 and its all-benzyl analogue (27).
• A synthetic route from D-glucose to D-myo-inositol-1, 4, 5-tris(dihydrogenphosphate): use of an unusual ene reaction and the Bu2SnCl2/Bu2SnH2 reagent
  作者：Derrick L.J. Clive、Xiao He、Maarten H.D. Postema、M. Jeffrey Mashimbye

  DOI：10.1016/s0040-4039(98)00792-8

  日期：1998.6

  d-Glucose was converted into the propargylsilane aldehyde 3, which underwent ring closure with retention of silicon, in the presence of camphorsulfonic acid, to give 5, and this was elaborated, via ketone 22, into 2, which had previously been transformed into d-myo-inositol-1, 4, 5-tris(dihydrogenphosphate). A crucial step in the synthesis is the stereoselective reduction of 22 with Bu2SnCl2/Bu2SnH2

  d-葡萄糖转化为炔丙基硅烷醛3，在樟脑磺酸存在下进行闭环并保留硅，得到5，然后通过酮22精制为2，之前已转化为d -肌醇-1，4，5-三（磷酸二氢）。合成中的关键步骤是用Bu 2 SnCl 2 / Bu 2 SnH 2选择性立体还原22，该试剂系统对生成赤道醇表现出强烈的偏好。
• Strong Aphicidal Activity of GlcNAc(β1→4)Glc Disaccharides: Synthesis, Physiological Effects, and Chitinase Inhibition
  作者：Christophe Dussouy、Laurent Bultel、Julien Saguez、Anas Cherqui、Mounia Khelifa、Eric Grand、Philippe Giordanengo、José Kovensky

  DOI：10.1002/chem.201200887

  日期：2012.8.6

  The synthesis of four GlcNAc(β1→4)Glc disaccharides containing 2‐O‐acetyl and/or 6‐sulfate groups was performed in high yields with total 1,2‐trans stereoselectivity. These disaccharides were evaluated as candidates for insect chitinase inhibition and aphicidal activity. All the compounds prepared displayed physiological effects on M. persicae aphids; however, the inhibition of chitinases of different

  含有2- O-乙酰基和/或6-硫酸根基团的四种GlcNAc（β1→4）Glc二糖的合成产率高，总1,2-反式立体选择性。这些二糖被评估为昆虫几丁质酶抑制和杀蚜活性的候选者。所制备的所有化合物对桃蚜的蚜虫均显示出生理作用。但是，根据微妙的结构特征，不同来源（细菌，真菌和蚜虫）的几丁质酶的抑制作用遵循不同的模式。