4'-methoxyphenyl 4,6-di-O-acetyl-2,3-dideoxy-1-O-β-D-erythro-hex-2-enopyranoside | 143134-83-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4'-methoxyphenyl 4,6-di-O-acetyl-2,3-dideoxy-1-O-β-D-erythro-hex-2-enopyranoside
• 英文别名: 4-methoxyphenyl 4,6-di-O-acetyl-2,3-dideoxy-1-O-α-D-erythro-hex-2-enopyranoside；4-methoxyphenyl 4, 6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside；p-methoxyphenyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythrohex-2-enopyranoside；[(2R,3S,6S)-3-acetyloxy-6-(4-methoxyphenoxy)-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 143134-83-2
• 化学式: C₁₇H₂₀O₇
• 分子量: 336.342
• InChiKey: XZKZMDQEIKXNPY-GVDBMIGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4'-methoxyphenyl 4,6-di-O-acetyl-2,3-dideoxy-1-O-β-D-erythro-hex-2-enopyranoside 在 N,N-二乙基苯胺 作用下， 反应 0.5h， 以80%的产率得到Acetic acid (2R,3S,4S)-2-acetoxymethyl-4-(2-hydroxy-5-methoxy-phenyl)-3,4-dihydro-2H-pyran-3-yl ester
  参考文献：
  名称：

  Balasubramanian, K. K.; Ramesh, N. G.; Pramanik, Animesh, Journal of the Chemical Society. Perkin transactions II, 1994, # 7, p. 1399 - 1402

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基苯酚 、 乙酰化葡萄烯糖 在 yttrium(III) trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以75%的产率得到4'-methoxyphenyl 4,6-di-O-acetyl-2,3-dideoxy-1-O-β-D-erythro-hex-2-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。
• Indium trichloride catalyzed glycosidation. An expeditious synthesis of 2,3-unsaturated glycopyranosides
  作者：Boga Sobhana Babu、Kalpattu Kuppuswamy Balasubramanian

  DOI：10.1016/s0040-4039(99)02266-2

  日期：2000.2

  Treatment of tri-O-acetyl-d-glucal 1 with various alcohols and phenols in the presence of InCl3/CH2Cl2 at ambient temperature gave the corresponding alkyl and aryl 2,3-unsaturated glycopyranosides in excellent yields with short reaction times and good anomeric selectivity.

  在环境温度下，在InCl 3 / CH 2 Cl 2存在下，用各种醇和酚处理三邻乙酰基-d-葡糖醛1，以极佳的收率和较短的反应时间得到了相应的烷基和芳基2,3-不饱和糖吡喃糖苷。和良好的异头选择性。
• 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。
• Yadav; Reddy; Murthy, Synlett, 2000, # 10, p. 1450 - 1451
  作者：Yadav、Reddy、Murthy、Kumar

  DOI：——

  日期：——