(2R,4aR,6S,7R,8S,8aR)-6-methoxy-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol | 222608-15-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (2R,4aR,6S,7R,8S,8aR)-6-methoxy-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 222608-15-3
• 化学式: C₂₁H₂₄O₆
• 分子量: 372.418
• InChiKey: FYUXMZUFURHCOX-ZWMUSQMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,4aR,6S,7R,8S,8aR)-6-methoxy-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol 、 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以91%的产率得到
  参考文献：
  名称：

  环戊糖基寡糖合成的扩环糖基化策略

  摘要：

  使用1，2-环丙烷化的糖作为糖基供体，并使用碳水化合物O-亲核试剂作为受体，进行一锅扩环糖基化反应，以提供吡喃糖和呋喃糖衍生物的庚烷己糖模拟物。通过采用分歧策略和迭代方案，该方法成功地扩展到了庚烷低聚糖的合成。

  DOI：

  10.1021/ol302677z

文献信息

• Gold(I)-Catalyzed Glycosylation with Glycosyl<i>ortho</i>-Alkynylbenzoates as Donors: General Scope and Application in the Synthesis of a Cyclic Triterpene Saponin
  作者：Yao Li、Xiaoyu Yang、Yunpeng Liu、Cunsheng Zhu、You Yang、Biao Yu

  DOI：10.1002/chem.200902548

  日期：2010.2.8

  coupling with the poorly nucleophilic amides gives satisfactory yields. Moreover, excellent α‐selective glycosylation with a 2‐deoxy sugar donor and β‐selective sialylation have been realized. Application of the present glycosylation protocol in the efficient synthesis of a cyclic triterpene tetrasaccharide have further demonstrated the versatility and efficacy of this new method, in that a novel chemoselective

  糖基邻炔基苯甲酸酯已成为在金（I）配合物如Ph 3 PAuOTf和Ph 3 PAuNTf 2催化下进行糖苷化的新一代供体（Tf ＝三氟甲磺酸盐）。这些供体种类繁多，包括2-脱氧糖和唾液酸供体，易于制备且易于保存。与醇类的糖苷偶联收率通常非常好；即使与不良亲核酰胺直接偶联也能获得令人满意的收率。此外，已经实现了具有2-脱氧糖供体的出色的α-选择性糖基化和β-选择性唾液酸化。本糖基化方案在环状三萜四糖高效合成中的应用进一步证明了这种新方法的多功能性和有效性，因为已实现了羧酸的新型化学选择性糖基化和新的单锅顺序糖基化序列。
• Stereoselective Synthesis of 2‐Deoxyglycosides from Glycals by Visible‐Light‐Induced Photoacid Catalysis
  作者：Gaoyuan Zhao、Ting Wang

  DOI：10.1002/anie.201800909

  日期：2018.5.22

  The direct, photoacid‐catalyzed synthesis of 2‐deoxyglycosides from glycals is reported. A series of phenol‐conjugated acridinium‐based organic photoacids were rationally designed, synthesized, and studied alongside the commercially available phenolic catalyst eosin Y. In the presence of such a photoacid catalyst and light, synthetic glycals were activated and coupled with a range of alcohols to afford

  据报道，由糖类直接，光酸催化合成了2-脱氧糖苷。与市售的酚催化剂曙红Y一起，合理设计，合成和研究了一系列基于酚共轭啶基的有机光酸。在这种光酸催化剂和光的存在下，合成糖被活化并与多种醇偶联以高收率和优异的α-选择性提供2-脱氧糖苷。
• Stereoselectivity investigation on glycosylation of oxazolidinone protected 2-amino-2-deoxy-d-glucose donors based on pre-activation protocol
  作者：Yiqun Geng、Li-He Zhang、Xin-Shan Ye

  DOI：10.1016/j.tet.2008.03.103

  日期：2008.5

  Diverse 2,3-oxazolidinone protected 2-amino-2-deoxy-d-glucose thioglycosides were prepared and studied as glycosyl donors at low temperature by BSM/Tf2O pre-activation protocol before the addition of glycosyl acceptors. The stereochemistry outcomes of a series of glycosylations were investigated. Different stereoselectivities of the coupling reactions were obtained, arising from the different protecting

  制备了各种2，3-恶唑烷酮保护的2-氨基-2-脱氧-d-葡萄糖硫代糖苷，并在添加糖基受体之前通过BSM / Tf 2 O预活化方​​案在低温下作为糖基供体进行了研究。研究了一系列糖基化的立体化学结果。由于恶唑烷酮供体中的不同保护基，导致偶联反应的立体选择性不同。4,6-二-O-苄基-N-苄基-恶唑烷酮保护的硫糖苷供体1c进行了糖基化，具有一般的β-异头异构体选择性，并且立体选择性也可能受到糖基化条件的影响。
• Photoinduced Glycosylation Using a Diarylthiophene as an Organo Lewis Photoacid Catalyst
  作者：Naoki Otani、Kohei Higashiyama、Hayato Sakai、Taku Hasobe、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1002/ejoc.202300287

  日期：2023.5.22

  Here reports an photoinduced glycosylation of trichloroacetimidate donors and several alcohols using 3,11‐dimethoxydinaphthothiophene as an organo Lewis photoacid catalyst upon long‐wavelength UV‐LED light (385 nm) irradiation. The reaction proceeded under mild reaction conditions smoothly to give the corresponding glycosides in good to high yields. In addition, the present glycosylation method was applicable to a wide range of trichloroacetimidate donors and acceptors. Furthermore, the dinaphthothiophene catalyst could be recovered and reused without any loss of efficiency. Moreover, this glycosylation method was applied successfully to the total synthesis of a biologically active natural product, cholesteryl 6‐O‐myristoyl‐α‐glucoside.

  摘要报告了以 3,11-二甲氧基二萘并噻吩为有机路易斯光酸催化剂，在长波紫外-LED 光（385 nm）照射下，对三氯乙酰亚氨酸供体和几种醇进行光诱导糖基化的研究。反应在温和的反应条件下顺利进行，以良好至高产率得到相应的糖苷。此外，本糖基化方法适用于多种三氯乙酰亚氨酸供体和受体。此外，二萘硫茚催化剂可回收和重复使用，而不会降低效率。此外，这种糖基化方法还成功地应用于生物活性天然产物胆甾烯基 6-O-肉豆蔻酰-α-葡萄糖苷的全合成。