phenyl 2,3-dideoxy-4,6-di-O-acetyl-β-D-erythro-hex-enopyranoside | 113019-34-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: phenyl 2,3-dideoxy-4,6-di-O-acetyl-β-D-erythro-hex-enopyranoside
• 英文别名: phenyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside；phenyl 4, 6-di-O-acetyl-2,3-dideoxy-1-O-α-D-erythro-hex-2-enopyranoside；phenoxyl 4, 6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside；[(2R,3S,6S)-3-acetyloxy-6-phenoxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 113019-34-4
• 化学式: C₁₆H₁₈O₆
• 分子量: 306.315
• InChiKey: YLYGQKOUMQKYKQ-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 2,3-dideoxy-4,6-di-O-acetyl-β-D-erythro-hex-enopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 (2R,3S,6S)-2-(hydroxymethyl)-6-phenoxy-3,6-dihydro-2H-pyran-3-ol
  参考文献：
  名称：

  由3,4,6-三-O-乙酰基-d-葡糖醛合成4-（4,6-二-O-苄基-2,3-二脱氧-β-d-赤型-己二-2-烯吡喃糖基）吡唑

  摘要：

  摘要3-（4,6-二-O-苄基-2,3-二脱氧-β-d-赤型-己基-2-烯吡喃糖基）-2,4-戊二酮及其类似物2-（4,6-di-由3,4,6-三-O-乙酰基-1,5制备的O-苄基-2,3-二脱氧-β-d-赤-己基-2-烯吡喃糖基）-1-苯基-1,3-丁二酮-脱水-2-脱氧-d-阿拉伯糖-己-1-烯醇（3,4,6-三-O-乙酰基-d-葡糖醛），与肼及其甲基，苯基，对甲苯基和室温下在乙醇中的对甲氧基苯基衍生物，以71–96％的收率提供一系列4-（4,6-二-O-苄基-2,3-二脱氧-β-d-赤-具有被上述基团游离或取代的N-1，和被甲基或苯基取代的C-5的六（2-吡喃并吡喃糖基）-3-甲基吡唑。1-苯基-1，3-丁二酮衍生物的反应是高度区域选择性的。这些新型化合物中的一些经催化氢化后，得到的4'，6'-di-O-脱保护的2'，3'-饱和化合物的产率为51-67％。标题化合物之一的乙酰水解/甲

  DOI：

  10.1016/s0008-6215(98)00059-7
• 作为产物：
  描述：

  乙酰化葡萄烯糖 、 苯酚 在 yttrium(III) trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以65%的产率得到phenyl 2,3-dideoxy-4,6-di-O-acetyl-β-D-erythro-hex-enopyranoside
  参考文献：
  名称：

  Y(OTf)3 as a highly efficient catalyst in Ferrier Rearrangement for the synthesis of O- and S-2,3-unsaturated glycopyranosides

  摘要：

  By using Y(OTf)(3) as the catalyst, a series of 2,3-unsaturated-glucosides have been synthesized from 3,4,6-tri-O-acetyl-D-glucal, 3,4-di-O-acetyl-L-rhamnal, and 3,4,6-tri-O-benzyl-D-glucal under mild reaction conditions in good yields with high anomeric selectivities. It was found that, in this reaction, 3,4,6-tri-O-benzyl-D-glucal behaved differently from the other two glucals when it was reacted with phenol, O-benzyl glucoside instead of O-phenyl glucoside formed as the sole product. An explanation is given for this phenomenon. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.08.092

文献信息

• A Highly Efficient Magnetic Iron(III) Nanocatalyst for Ferrier Rearrangements
  作者：Youxian Dong、Zekun Ding、Hong Guo、Le Zhou、Nan Jiang、Heshan Chen、Saifeng Qiu、Xiaoxia Xu、Jianbo Zhang

  DOI：10.1055/s-0037-1611855

  日期：2019.7

  A novel and highly efficient magnetic Fe3O4@C@Fe(III) core–shell catalyst, in which the carbon shell was prepared from lotus leaf, was fabricated. This nanocatalyst was successfully applied in the synthesis of a series of 2,3-unsaturated O-glycosides in excellent yields and with high selectivity, especially in the case of 2-halo O-glycosides, which differ in reactivity from nonsubstituted O-glycosides

  制备了一种新型高效的磁性 Fe3O4@C@Fe(III) 核壳催化剂，其中碳壳由荷叶制备。该纳米催化剂成功地应用于合成一系列 2,3-不饱和 O-糖苷，收率高，选择性高，特别是在反应性与未取代 O-糖苷不同的 2-卤代 O-糖苷的情况下，但以前几乎没有探索过。此外，通过施加外部磁力，催化剂可以很容易地从反应中分离出来，并且至少重复使用五次，而不会显着降低产品的产率。此外，该反应在克级规模上很容易进行，这为未来的应用提供了广阔的前景。
• Highly Stereoselective Synthesis of Pseudoglycals via Yb(OTf)₃ Catalyzed Ferrier Glycosylation
  作者：Mohamed Takhi、Adel A.-H. Abdel-Rahman、Richard R. Schmidt

  DOI：10.1055/s-2001-11387

  日期：——

  The reaction of tri-O-acetyl-d-glucal with various alcohols and thiols was effectively promoted by a catalytic amount of Yb(OTf)3 to produce a variety of pseudoglycals via Ferrier rearrangement in excellent yields and anomeric selectivity.

  三-O-醋酸基-d-glucal与多种醇和硫醇的反应在催化量的Yb(OTf)3的有效促进下，通过Ferrier重排反应生成多种伪糖苷，产率高且具有优良的异构体选择性。
• Phenolic ferrier reaction and its application to the natural product synthesis
  作者：Toshiro Noshita、Takeyoshi Sugiyama、Yoshiharu Kitazumi、Takayuki Oritani

  DOI：10.1016/0040-4039(94)88297-5

  日期：1994.10

  Aryl O-Δ2-glycosides were synthesized by Ferrier reaction. p-Methoxyphenyl group was oxidatively removed with Ag(DPAH)2.

  芳ø -Δ 2 -glycosides通过Ferrier的反应合成。用Ag（DPAH）2氧化除去对甲氧基苯基。
• A convenient synthesis of pseudoglycosides via a Ferrier-type rearrangement using metal-free H3PO4 catalyst
  作者：Bala Kishan Gorityala、Shuting Cai、Rujee Lorpitthaya、Jimei Ma、Kalyan Kumar Pasunooti、Xue-Wei Liu

  DOI：10.1016/j.tetlet.2008.11.103

  日期：2009.2

  A mild and efficient synthesis of pseudoglycals has been developed using a metal-free catalytic system. Phosphoric acid proved to be an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-D-glycal to 2,3-unsaturated O-glycosides. A wide range of alcohols including naturally bioactive compounds could be coupled with the glycal to give the desired products in good to excellent yields and with high levels of alpha-selectivity. (C) 2008 Elsevier Ltd. All rights reserved.
• ZnBr₂-Catalyzed and Microwave-Assisted Synthesis of 2,3-Unsaturated Glucosides of Hindered Phenols and Alcohols
  作者：D. James Bound、B. K. Bettadaiah、P. Srinivas

  DOI：10.1080/00397911.2014.909490

  日期：2014.9.2