4'-methoxyphenyl 4-O-acetyl-2,3,6-trideoxy-1-O-α-L-erythro-hex-2-enopyranoside | 160956-79-6

• 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-O-acetyl-2,3,6-trideoxy-1-O-α-L-erythro-hex-2-enopyranoside
• 英文别名: 4-methoxyphenyl 4-O-acetyl-6-deoxy-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside；p-methoxyphenyl 4-O-acetyl-6-deoxy-2,3-dideoxy-α-L-erythrohex-2-enopyranoside；[(2S,3R,6S)-6-(4-methoxyphenoxy)-2-methyl-3,6-dihydro-2H-pyran-3-yl] acetate
• CAS: 160956-79-6
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: NNSFUPZCKPGWBL-VQISRLSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4'-methoxyphenyl 4-O-acetyl-2,3,6-trideoxy-1-O-α-L-erythro-hex-2-enopyranoside 在 咪唑 、 甲醇 、 manganese(IV) oxide 、 pyridine-2,6-dicarboxylic acid, Ag(II) chelate 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.5h， 生成 (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-methyl-2,3-dihydropyran-6-one
  参考文献：
  名称：

  酚类递质反应及其在天然产物合成中的应用

  摘要：

  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。

  DOI：

  10.1016/0040-4039(94)88297-5
• 作为产物：
  描述：

  4-甲氧基苯酚 、 3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 samarium(III) trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以64%的产率得到4'-methoxyphenyl 4-O-acetyl-2,3,6-trideoxy-1-O-α-L-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Sm(OTf)3 as a highly efficient catalyst for the synthesis of 2,3-unsaturated O- and S-pyranosides from glycals and the temperature-dependent formation of 4-O-acetyl-6-deoxy-2,3-unsaturated S-pyranosides and 4-O-acetyl-6-deoxy-3-alkylthio glycals

  摘要：

  By using Sm(OTf)(3) as the catalyst, synthesis of 2,3-unsaturated-glycosides has been performed. A series of 2,3-unsaturated glycosides were obtained from 3,4,6-tri-O-acetyl-D-glucal or 3,4-di-O-acetyl-L-rhamnal under mild reaction conditions in good yield and high anomeric selectivity. It was found that under certain conditions, reaction of 3,4-di-O-acetyl-L-rhamnal with thiol leads to temperature-dependent formation of C-1-S and C-3-S product. A temperature-dependent profile of the yield of these two products is given. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.09.060

文献信息

• Y(OTf)3 as a highly efficient catalyst in Ferrier Rearrangement for the synthesis of O- and S-2,3-unsaturated glycopyranosides
  作者：Peiran Chen、Shan Li

  DOI：10.1016/j.tetlet.2014.08.092

  日期：2014.10

  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.
• Noshita, Toshiro; Sugiyama, Takeyoshi; Kitazumi, Yoshiharu, Bioscience, Biotechnology and Biochemistry, 1995, vol. 59, # 11, p. 2052 - 2055
  作者：Noshita, Toshiro、Sugiyama, Takeyoshi、Kitazumi, Yoshiharu、Oritani, Takayuki

  DOI：——

  日期：——