3,4,5-trimethoxyphenyl 2,3,4-tri-O-phenoxyacetyl-6-O-(2,3-di-O-phenoxyacetyl-β-D-erythro-apiofuranosyl)-β-D-glucopyranoside | 209113-74-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4,5-trimethoxyphenyl 2,3,4-tri-O-phenoxyacetyl-6-O-(2,3-di-O-phenoxyacetyl-β-D-erythro-apiofuranosyl)-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-2-[[(2R,3R,4R)-4-(hydroxymethyl)-3,4-bis[(2-phenoxyacetyl)oxy]oxolan-2-yl]oxymethyl]-4,5-bis[(2-phenoxyacetyl)oxy]-6-(3,4,5-trimethoxyphenoxy)oxan-3-yl] 2-phenoxyacetate
• CAS: 209113-74-6
• 化学式: C₆₀H₆₀O₂₃
• 分子量: 1149.12
• InChiKey: RSYFJUOVNLKTBQ-CQCXOHBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  83
• 可旋转键数：
  34
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  263
• 氢给体数：
  1
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  (E)-3,4-di-O-acetylcaffeoyl chloride 、 3,4,5-trimethoxyphenyl 2,3,4-tri-O-phenoxyacetyl-6-O-(2,3-di-O-phenoxyacetyl-β-D-erythro-apiofuranosyl)-β-D-glucopyranoside 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以77%的产率得到3,4,5-trimethoxyphenyl 2,3,4-tri-O-phenoxyacetyl-6-O-(2,3-di-O-phenoxyacetyl-5-O-(3,4-di-O-acetylcaffeoyl)-β-D-erythro-apiofuranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  合成kelampayosides A和B的快速途径

  摘要：

  化学选择性NIS /猫。TfOH介导的乙基2,3,4-三-O-苯甲酰基-1-硫代-β-d-吡喃葡萄糖苷（13）与乙基2,3-二-O-乙酰基-5-O-苄基-1-硫代-的糖基化作用αβ-d-赤型-呋喃呋喃糖苷（4a）以优异的产率得到二聚体14。BF 3 •Et 2 O催化的α-三氯乙酰亚胺酸酯31的缩合反应（从14步可分两个步骤进行）与3,4,5-三甲氧基苯酚生成β-连接的衍生物32，然后脱保护得到KelampayosideA。保护基的操作为32和所得的后续caffeoylation 36接着进行脱保护，得到Kelampayoside B.图选项

  DOI：

  10.1016/s0040-4020(99)00527-x
• 作为产物：
  描述：

  3,4,5-三甲氧基苯酚 在 palladium on activated charcoal 吡啶 、 三氟化硼乙醚 、 氢气 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 异丙醇 为溶剂， 生成 3,4,5-trimethoxyphenyl 2,3,4-tri-O-phenoxyacetyl-6-O-(2,3-di-O-phenoxyacetyl-β-D-erythro-apiofuranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 3,4,5-trimethoxyphenyl 5″-O-caffeoyl-β-d-erythro-apiofuranosyl-(1→6)-β-d-glucopyranoside: Kelampayoside B

  摘要：

  Chemoselective NIS/ cat. TfOH-mediated glycosylation of ethyl 2,3,4-tri-O-benzoyl-1-thio-beta-D-glucopyranoside (4) with ethyl 2,3-di-O-acetyl-5-O-benzyl-1-thio-alpha/beta-D-erythro-apiofuranoside (3) gave dimer 5 in an excellent yield. BF3Et2O-catalysed condensation of the alpha-trichloroacetimidate 18, accessible in two steps from 5, with 3,4,5-trimethoxyphenol gave beta-linked derivative 19 which could be transformed in five steps into the title compound. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00673-x

文献信息

• Synthesis of 3,4,5-trimethoxyphenyl 5″-O-caffeoyl-β-d-erythro-apiofuranosyl-(1→6)-β-d-glucopyranoside: Kelampayoside B
  作者：Howard I. Duynstee、Martijn C. de Koning、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1016/s0040-4039(98)00673-x

  日期：1998.6

  Chemoselective NIS/ cat. TfOH-mediated glycosylation of ethyl 2,3,4-tri-O-benzoyl-1-thio-beta-D-glucopyranoside (4) with ethyl 2,3-di-O-acetyl-5-O-benzyl-1-thio-alpha/beta-D-erythro-apiofuranoside (3) gave dimer 5 in an excellent yield. BF3Et2O-catalysed condensation of the alpha-trichloroacetimidate 18, accessible in two steps from 5, with 3,4,5-trimethoxyphenol gave beta-linked derivative 19 which could be transformed in five steps into the title compound. (C) 1998 Elsevier Science Ltd. All rights reserved.
• An expeditious route to the synthesis of kelampayosides A and B
  作者：Howard I. Duynstee、Martijn C. de Koning、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1016/s0040-4020(99)00527-x

  日期：1999.8

  Chemoselective NIS/ cat. TfOH-mediated glycosylation of ethyl2,3,4-tri-O-benzoyl-1-thio-β-d-glucopyranoside (13) with ethyl2,3-di-O-acetyl-5-O-benzyl-1-thio-αβ-d-erythro-apiofuranoside (4a) gave dimer14 in an excellent yield. BF3•Et2O-catalysed condensation of the α-trichloroacetimidate31, accessible in two steps from14, with 3,4,5-trimethoxyphenol gave β-linked derivative32 followed by deprotection

  化学选择性NIS /猫。TfOH介导的乙基2,3,4-三-O-苯甲酰基-1-硫代-β-d-吡喃葡萄糖苷（13）与乙基2,3-二-O-乙酰基-5-O-苄基-1-硫代-的糖基化作用αβ-d-赤型-呋喃呋喃糖苷（4a）以优异的产率得到二聚体14。BF 3 •Et 2 O催化的α-三氯乙酰亚胺酸酯31的缩合反应（从14步可分两个步骤进行）与3,4,5-三甲氧基苯酚生成β-连接的衍生物32，然后脱保护得到KelampayosideA。保护基的操作为32和所得的后续caffeoylation 36接着进行脱保护，得到Kelampayoside B.图选项