(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)phenylacetylene | 113794-27-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)phenylacetylene
• 英文别名: α-1,5-anhydro-1-C-(2-phenylethynyl)-2,3,4,6-tetra-O-benzyl-D-glucitol；(2R,3R,4R,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(phenylethynyl)tetrahydro-2H-pyran；(2R,3S,4R,5R,6R)-2-(2-phenylethynyl)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 113794-27-7
• 化学式: C₄₂H₄₀O₅
• 分子量: 624.777
• InChiKey: DOJBYTBKIMAHAT-QBLDGPCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  47
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)phenylacetylene 在 Lindlar's catalyst 喹啉 、 sodium tetrahydroborate 、 氢气 、 臭氧 作用下， 以 乙醇 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 14.0h， 生成 (2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)methanol
  参考文献：
  名称：

  Alkynylation of mixed acetals with organotin acetylides

  摘要：

  DOI：

  10.1021/ja00216a025
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl 4-nitrobenzoate 在 氢溴酸 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 0.58h， 生成 (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)phenylacetylene
  参考文献：
  名称：

  Alkynylation of mixed acetals with organotin acetylides

  摘要：

  DOI：

  10.1021/ja00216a025

文献信息

• Direct <i>C</i>-Glycosylation of Organotrifluoroborates with Glycosyl Fluorides and Its Application to the Total Synthesis of (+)-Varitriol
  作者：Jing Zeng、Seenuvasan Vedachalam、Shaohua Xiang、Xue-Wei Liu

  DOI：10.1021/ol102473k

  日期：2011.1.7

  C-glycosides via BF3·Et2O promoted coupling of organotrifluoroborates and glycosyl fluorides is reported. The application of this method was further demonstrated by the concise and efficient total synthesis of (+)-varitriol in only seven steps.

  据报道，通过BF 3 ·Et 2 O促进了有机三氟硼酸酯和糖基氟化物的偶联，采用了温和，立体选择性和快速的方法访问炔基和烯基C-糖苷。该方法的应用通过仅七个步骤的简明有效的全合成（+）-varitriol进一步得到了证明。
• Synthesis of Polyhydroxylated Pyrano-Pyrrole Derivatives from Carbohydrate Precursors
  作者：Sébastien Naud、Muriel Pipelier、Guillaume Viault、Ané Adjou、François Huet、Stéphanie Legoupy、Anne-Marie Aubertin、Michel Evain、Didier Dubreuil

  DOI：10.1002/ejoc.200700102

  日期：2007.7

  The efficient synthesis of novel polyhydroxy-tetrahydropyrano-pyrroles from acetylenic carbohydrate precursors in three to four steps is described. The methodology involves, as key steps, the ring contraction of pyridazine intermediates obtained by an inverse-demand Diels–Alder reaction and subsequent intramolecular lactonization. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  描述了从炔烃前体分三到四步有效合成新型多羟基-四氢吡喃-吡咯。该方法包括作为关键步骤，通过逆需求 Diels-Alder 反应和随后的分子内内酯化获得哒嗪中间体的环收缩。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Highly Stereoselective <scp>C‐Glycosylation</scp> by Photocatalytic Decarboxylative Alkynylation on Anomeric Position: A Facile Access to Alkynyl <scp> <i>C</i> ‐Glycosides </scp>
  作者：KaiLin Lu、Yingying Ma、Shihui Liu、Shixun Guo、Yongqiang Zhang

  DOI：10.1002/cjoc.202100438

  日期：2022.3.15

  The highly stereoselective synthesis of diverse medicinally valuable alkynyl C-glycosides under mild and green reaction conditions remains a great challenge. Herein, we wish to report a visible-light induced photocatalytic decarboxylative alkynylation approach. By utilizing an iridium photocatalyst in the presence of visible light, glycosyl radicals are in-situ generated via the decarboxylation of

  在温和和绿色的反应条件下高度立体选择性地合成多种具有药用价值的炔基C-糖苷仍然是一个巨大的挑战。在此，我们希望报告一种可见光诱导的光催化脱羧炔基化方法。通过在可见光下使用铱光催化剂，糖基自由基通过异头酸的脱羧作用原位产生，并与多种乙炔基苯并氧杂环戊烷（EBX）有效偶联，从而可以轻松合成多种炔基C-糖苷产率中等至高，并具有优异的非对映选择性。
• Direct <i>C</i>-Glycosylation by Indium-Mediated Alkynylation on Sugar Anomeric Position
  作者：Nadège Lubin-Germain、Jean-Pierre Baltaze、Alexis Coste、Agnès Hallonet、Hugo Lauréano、Grégory Legrave、Jacques Uziel、Jacques Augé

  DOI：10.1021/ol7029257

  日期：2008.3.1

  Indium-mediated alkynylation reaction was studied for the direct preparation of C-glycosides. Easily available starting sugar derivatives with an acetyl group at the anomeric position were tested as electrophiles toward alkynylindium reagents under Barbier conditions. Good yields and stereoselectivities were observed during the reaction. The alkynylation was applied to the synthesis of an alpha-(1 -> 6)-C-disaccharide analogue of isomaltoside.
• Tolstikov, G. A.; Prokhorova, N. A.; Spivak, A. Yu., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 10, p. 1858 - 1863
  作者：Tolstikov, G. A.、Prokhorova, N. A.、Spivak, A. Yu.、Khalilov, L. M.、Sultanmuratova, V. R.

  DOI：——

  日期：——