Kelampayoside A; 3,4,5-三甲氧基苯基 6-O-D-芹糖-beta-D-呋喃糖基-beta-D-葡萄糖苷 | 87562-76-3

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: Kelampayoside A; 3,4,5-三甲氧基苯基 6-O-D-芹糖-beta-D-呋喃糖基-beta-D-葡萄糖苷
• 中文别名: KelampayosideA;3,4,5-三甲氧基苯基6-O-D-芹糖-beta-D-呋喃糖基-beta-D-葡萄糖苷；3,4,5-三甲氧基苯基6-O-D-芹糖-BETA-D-呋喃糖基-BETA-D-葡萄糖苷；3,4,5-三甲氧基苯基 6-O-D-芹糖-BETA-D-呋喃糖基-BETA-D-葡萄糖苷
• 英文名称: kelampayoside A
• 英文别名: (3,4,5-trimethoxyphenyl)-1-O-β-D-apiofuranosyl-(1->6)-β-D-glucopyranoside；3,4,5-trimethoxyphenyl 1-O-β-D-apiofuranosyl-(1->6)-O-β-D-glucopyranoside；3,4,5-trimethoxyphenyl-1-O-β-D-apiofuranosyl-(1->6)-O-β-D-glucopyranoside；3,4,5-trimethoxyphenol 1-O-β-D-apiofuranosyl-(1->6)-β-D-glucopyranoside；3,4,5-trimethoxyphenyl 1-O-β-D-apiofuranosyl-(1->6)-β-D-glucopyranoside；3,4,5-trimethoxyphenol 1-O-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside；(2R,3S,4S,5R,6S)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-(3,4,5-trimethoxyphenoxy)oxane-3,4,5-triol
• CAS: 87562-76-3
• 化学式: C₂₀H₃₀O₁₃
• 分子量: 478.45
• InChiKey: CKGKQISENBKOCA-FHXQZXMCSA-N

物化性质

• 沸点：
  735.9±60.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)
• 物理描述：
  Solid
• 熔点：
  132-134°C

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  186
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苯酚 在 palladium on activated charcoal 三氟化硼乙醚 、 氢气 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 异丙醇 为溶剂， 生成 Kelampayoside A; 3,4,5-三甲氧基苯基 6-O-D-芹糖-beta-D-呋喃糖基-beta-D-葡萄糖苷
  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

• 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
• Three New Hemiterpene Glycosides from Ilex macropoda.
  作者：Hiroyuki FUCHINO、Hironori TACHIBANA、Nobutoshi TANAKA

  DOI：10.1248/cpb.45.1533

  日期：——

  Phytochemical studies of Ilex macropoda led to the isolation of three new hemiterpene glycosides, 4-β-D-glucopyranosyloxy-5-hydroxyprenyl caffeate (aohada-glycoside A), 5-caffeoyloxy-4-β-D-glucopyranosyloxyprenyl alcohol (aohada-glycoside B), 4-(6-O-caffeoyl-β-D-glucopyranosyloxy)-5-hydroxyprenyl caffeate (aohada-glycoside C), together with betulin, acetyl ursolic acid, ilexosides XVII and XVIII, and 3, 4, 5-trimethoxyphenol β-D-5-O-caffeoyl-apiofuranosyl-(1→6)-β-D-glucopyranoside from the bark. Rotundioic acid, ursolic acid, ilexosides II and XXX, ziyu-glycoside I and rutin were also isolated from fresh leaves, and 3, 5-dicaffeoylquinic acid and 3, 4-dicaffeoylquinic acid from the wood.

  通过对大戟科植物的植物化学研究，分离出了三种新的半萜苷，即 4-β-D-Glucopyranosyloxy-5-hydroxyprenyl caffeate（aohada-glycoside A）、5-caffeoyloxy-4-β-D-glucopyranosyloxyprenyl alcohol（aohada-glycoside B）、4-(6-O-caffeoyl-β-D-glucopyranosyloxy)-5-hydroxyprenyl caffeate (aohada-glycoside C)，以及来自树皮的 betulin、acetyl ursolic acid、ilexosides XVII 和 XVIII 以及 3, 4, 5-trimethoxyphenol β-D-5-O-caffeoyl-apiofuranosyl-(1→6)-β-D-glucopyranoside 。此外，还从鲜叶中分离出 Rotundioic acid、熊果酸、ilexosides II 和 XXX、ziyu-glycoside I 和芦丁，从木材中分离出 3，5-二咖啡酰奎宁酸和 3，4-二咖啡酰奎宁酸。
• 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.