2-iodo-3,5-bis(phenylmethoxy)benzenemethanol | 934243-80-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-iodo-3,5-bis(phenylmethoxy)benzenemethanol
• 英文别名: (3,5-bis-benzyloxy-2-iodo-phenyl)-methanol；3,5-dibenzyloxy-2-iodobenzyl alcohol
• CAS: 934243-80-8
• 化学式: C₂₁H₁₉IO₃
• 分子量: 446.285
• InChiKey: AMUYBEIAPJUIDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-iodo-3,5-bis(phenylmethoxy)benzenemethanol 在 吡啶 、 4-二甲氨基吡啶 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 palladium 10% on activated carbon 、 氢气 、 tri-n-butylamine hydrofluoride 、 二异丁基氢化铝 、 碳酸氢钠 、 tetra-n-butylammoniumfluoride trihydrate 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 234.58h， 生成 (1S,4a'R,7'R,8'R,8a'R)-2',2'-di-tert-butyl-5,7,7'-tris(methoxymethoxy)-4a',7',8',8a'-tetrahydro-3H,4'H-spiro[isobenzofuran-1,6'-pyrano[3,2-d][1,3,2]dioxasilin]-8'-yl (9Z,12Z)-octadeca-9,12-dienoate
  参考文献：
  名称：

  Synthesis and antifungal properties of papulacandin derivatives

  摘要：

  一种靶向β-(1,3)-D-葡聚糖合酶的抗真菌剂 papulacandin D 的衍生物已合成并进行了活性测试。papulacandin D 结构包含一个具有挑战性的苯环螺环糖醚单元，该单元是通过一种钯催化的糖环硅醇酸酯和芳基碘化物的交叉偶联反应引入的，随后进行氧化螺环糖醚化反应。制备了四种不同的变体，其在酰基侧链的性质、长度以及双键的数量和立体化学方面有所不同。基于棕榈酸和亚油酸的侧链的衍生物显示出中等生物活性。

  DOI：

  10.3762/bjoc.8.82
• 作为产物：
  描述：

  3,5-二羟基苯甲酸 在 N-碘代丁二酰亚胺 、 lithium aluminium tetrahydride 、 硫酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 氯仿 、 丙酮 为溶剂， 反应 54.5h， 生成 2-iodo-3,5-bis(phenylmethoxy)benzenemethanol
  参考文献：
  名称：

  Synthesis and antifungal properties of papulacandin derivatives

  摘要：

  一种靶向β-(1,3)-D-葡聚糖合酶的抗真菌剂 papulacandin D 的衍生物已合成并进行了活性测试。papulacandin D 结构包含一个具有挑战性的苯环螺环糖醚单元，该单元是通过一种钯催化的糖环硅醇酸酯和芳基碘化物的交叉偶联反应引入的，随后进行氧化螺环糖醚化反应。制备了四种不同的变体，其在酰基侧链的性质、长度以及双键的数量和立体化学方面有所不同。基于棕榈酸和亚油酸的侧链的衍生物显示出中等生物活性。

  DOI：

  10.3762/bjoc.8.82

文献信息

• De novo synthesis of a galacto-papulacandin moiety via an iterative dihydroxylation strategy
  作者：Md. Moinuddin Ahmed、George A. O’Doherty

  DOI：10.1016/j.tetlet.2005.04.073

  日期：2005.6

  A short and highly efficient route to both the pyranose and furanose forms of a galacto-papulacandin ring system has been developed. The key to the overall transformation is the sequential two osmium-catalyzed dihydroxylation reactions of substituted 2,4-dienone. The resulting tetrol can be efficiently transformed into the two spiroketal moieties of galacto-papulacandin, which can also be inter-converted

  已经开发出短促且高效的途径，以半乳糖-帕普拉丹定环系统的吡喃糖和呋喃糖形式。整体转化的关键是取代的2，4-二烯酮连续两次two催化的二羟基化反应。所得的四氢萘酚可有效地转化为半乳糖-帕普拉汀的两个螺酮基部分，它们也可通过酸催化的平衡相互转化。
• Cross-Coupling Reaction of Saccharide-Based Alkenyl Boronic Acids with Aryl Halides: The Synthesis of Bergenin
  作者：Kamil Parkan、Radek Pohl、Martin Kotora

  DOI：10.1002/chem.201304304

  日期：2014.4.7

  isolated yields was achieved. Both pinacol boronates were tested in a series of cross‐coupling reactions under Suzuki–Miyaura cross‐coupling conditions to obtain the corresponding aryl, heteroaryl, and alkenyl derivatives in high isolated yields. This methodology was applied to the formal synthesis of the glucopyranoside moiety of papulacandin D and the first total synthesis of bergenin.

  一种方便的合成途径使d -glucal和d -galactal频哪醇硼酸酯，以良好的产率分离出来制备达到了。两种频哪醇硼酸酯都在Suzuki–Miyaura交叉偶联条件下进行了一系列交叉偶联反应测试，从而以高分离产率获得了相应的芳基，杂芳基和烯基衍生物。该方法学适用于木瓜素D的吡喃葡萄糖苷部分的正式合成和佛手素的首次全合成。
• Total Synthesis of Papulacandin D
  作者：Scott E. Denmark、Christopher S. Regens、Tetsuya Kobayashi

  DOI：10.1021/ja070071z

  日期：2007.3.1

  A total synthesis of the antifungal agent papulacandin D is reported. The molecule is representative of a large class of C-aryl glycosides that exhibit significant antifungal activity. The synthetic strategy bifurcates the molecule into two nearly equal subunits, the arylglycoside and 18-carbon fatty acid side chain. The key strategic transformations are (1) the palladium catalyzed, organosilanolate-based cross-coupling of a protected glucal silanol and (2) a catalytic enantioselective allylation of a dienal using allyltrichlorosilane. The synthesis was accomplished in 31 steps overall from commercial starting materials to afford over 50 mg of the natural product.
• Total synthesis of (+)-papulacandin D
  作者：Scott E. Denmark、Tetsuya Kobayashi、Christopher S. Regens

  DOI：10.1016/j.tet.2010.03.093

  日期：2010.6

  A total synthesis of (+)-papulacandin D has been achieved in 31 steps, in a 9.2% overall yield from commercially available materials. The synthetic strategy divided the molecule into two nearly equal sized subunits, the spirocyclic C-arylglycopyranoside and the polyunsaturated fatty acid side-chain. The C-arylglycopyranoside was prepared in 11 steps in a 30% overall yield from triacetoxyglucal. The fatty acid side-chain was also prepared in 11 steps in a 30% overall yield from geraniol. The key strategic transformations in the synthesis are: (1) a palladium-catalyzed, organosilanolate-based cross-coupling reaction of a dimethylglucal-silanol with an electron-rich and sterically hindered aromatic iodide and (2) a Lewis-base catalyzed, enantioselective allylation reaction of a dienal and allyltrichlorosilane. A critical element in the successful execution of the synthesis was the development of a suitable protecting group strategy that satisfied a number of stringent criteria. (C) 2010 Elsevier Ltd. All rights reserved.