2-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)acetophenon | 85422-88-4

• 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)acetophenon
• 英文别名: 2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)acetophenone；1-phenyl-2-(3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)ethan-1-one；1-phenyl-2-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]ethanone
• CAS: 85422-88-4
• 化学式: C₄₂H₄₂O₆
• 分子量: 642.792
• InChiKey: BSGCRVNJWIKYIN-CTLZPSQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)acetophenon 在 吡啶 、 4-二甲氨基吡啶 、 二异丁基氢化铝 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Versatile Glycosyl Sulfonates in β‐Selective C‐Glycosylation

  摘要：

  AbstractC‐Glycosides are both a common motif in many bioactive natural products and important glycoside mimetics. We demonstrate that activating a hemiacetal with a sulfonyl chloride, followed by treating the resultant glycosyl sulfonate with an enolate results in the stereospecific construction of β‐linked C‐glycosides. This reaction tolerates a range of acceptors and donors, including disaccharides. The resulting products can be readily derivatized into C‐glycoside analogues of β‐glycoconjugates, including C‐disaccharide mimetics.

  DOI：

  10.1002/anie.201914221
• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 三氟化硼乙醚 作用下， 反应 0.08h， 生成 2-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)acetophenon
  参考文献：
  名称：

  Schmidt, Richard R.; Hoffmann, Michael, Angewandte Chemie, 1983, vol. 95, # 5, p. 417 - 418

  摘要：

  DOI：

文献信息

• Gold(<scp>i</scp>)-catalyzed C-glycosylation of glycosyl ortho-alkynylbenzoates: the role of the moisture sequestered by molecular sieves
  作者：Xiaoping Chen、Qiaoling Wang、Biao Yu

  DOI：10.1039/c6cc07218f

  日期：——

  C-Glycosylation of glycosyl ortho-hexynylbenzoates with allyltrimethylsilane or silyl enol ethers could proceed smoothly under the catalysis of Ph₃PAuNTf₂, wherein the moisture sequestered by the molecular sieves ensured the gold(i)-catalytic cycle.

  将glycosyl ortho-hexynylbenzoates与allyltrimethylsilane或硅烯醚进行C-糖基化反应，可在Ph3PAuNTf2的催化下顺利进行，其中分子筛吸附的水分确保了金（i）催化循环的进行。
• The Mukaiyama type aldol reaction for the synthesis of <i>trans</i>-2,6-disubstituted tetrahydropyrans: synthesis of diospongin A and B
  作者：Yada Bharath、Utkal Mani Choudhury、N. Sadhana、Debendra K. Mohapatra

  DOI：10.1039/c9ob01549c

  日期：——

  An efficient synthesis protocol for the preparation of trans-2,6-disubstituted tetrahydropyrans by the reaction of 1-phenyl-1-triemthylsiloxyethylene with six membered cyclic hemiacetals in the presence of iodine is developed. This reaction proceeds smoothly under mild conditions employing a catalytic amount of molecular iodine. The feature of this novel conversion includes milder reaction conditions

  开发了一种有效的合成方案，用于在碘存在下通过1-苯基-1-三乙基甲硅烷氧基乙烯与六元环半缩醛的反应来制备反式2,6-二取代的四氢吡喃。该反应在温和条件下使用催化量的分子碘可以顺利进行。这种新型转化的特征包括较温和的反应条件，较宽的底物范围，官能团耐受性和良好的非对映选择性。本方法的效率和实用性成功地展示了双皂甙A和B的全合成，收率很高。
• Reactions of glycosyl fluorides. Synthesis of C-glycosides
  作者：K. C. Nicolaou、Roland E. Dolle、Alexander Chucholowski、Jared L. Randall

  DOI：10.1039/c39840001153

  日期：——

  Glycosyl fluorides were found to react with a number of nucleophilic reagents with or without catalysis leading to a variety of C-glycosides and related compounds.

  发现糖基氟化物在催化作用或不催化作用下与许多亲核试剂反应，从而导致多种C-糖苷和相关化合物。
• Hoffmann, Michael G.; Schmidt, Richard R., Liebigs Annalen der Chemie, 1985, # 12, p. 2403 - 2419
  作者：Hoffmann, Michael G.、Schmidt, Richard R.

  DOI：——

  日期：——
• Allevi, Pietro; Anastasia, Mario; Ciuffreda, Pierangela, Journal of the Chemical Society. Perkin transactions I, 1989, p. 1275 - 1280
  作者：Allevi, Pietro、Anastasia, Mario、Ciuffreda, Pierangela、Fiecchi, Alberto、Scala, Antonio

  DOI：——

  日期：——