methyl (2,3-di-O-benzoyl-4-O-methyl-α-D-gucopyranosyl trichloroacetamidate)uronate | 372518-28-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2,3-di-O-benzoyl-4-O-methyl-α-D-gucopyranosyl trichloroacetamidate)uronate
• 英文别名: methyl (2S,3S,4S,5R,6R)-4,5-dibenzoyloxy-3-methoxy-6-(2,2,2-trichloroethanimidoyl)oxyoxane-2-carboxylate
• CAS: 372518-28-0
• 化学式: C₂₄H₂₂Cl₃NO₉
• 分子量: 574.799
• InChiKey: KBQHJWHFXQKNBJ-UDDBWUTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl (2,3-di-O-benzoyl-4-O-methyl-α-D-gucopyranosyl trichloroacetamidate)uronate 在 palladium on activated charcoal 吡啶 、 三氟甲磺酸三甲基硅酯 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 methyl (2,3-di-O-benzoyl-4-O-methyl-β-D-glucopyranosyl)uronate-(1->6)-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Syntheses of model compounds related to an antigenic epitope in pectic polysaccharides from Bupleurum falcatum L.

  摘要：

  Stereocontrolled syntheses of model compounds related to a category of the major antigenic epitope against anti-bupleurum 2IIc/PG-1-IgG from an anti-ulcer pectic polysaccharide are described. Glycosylation of the glucuronic acid donors methyl(2,3-di-O-benzoyl-4-O-methyl-alpha -D-glucopyranosyl trichloroacetimidate)uronate and methyl (2,3-di-O-benzoyl-4-O-methyl-beta -D-glucopyranosyl)uronate-(1 -->6)-2,3,4-tri-O-benzoyl-alpha -D-galactopyranosyl trichloroacetimidate with the common acceptor 2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-beta -D-galactopyranoside in the presence of trimethylsilyl triflate (TMSOTf) gave the desired di- and trisaccharide derivatives. Furthermore the products were transformed into the oligo-valent clustering saccharides, N,N',N"-tri-{5-[4-O-methyl-beta -D-glucopyranosyluronic acid-(1 --> 6)-beta -D-galactopyranosyloxy]pentylcarbonylaminoethyl}-1,3,5-benzenetriamide and N,N',N"-tri-{5-[4-O-methyl-beta -D-glucopyranosyluronic acid (1 --> 6)-beta -D-galactopyranosyl-(1 --> 6)-beta -D-galactopyranosyloxy]pentylcarbonylaminoethyl}-1,3,5-benzenetriamide. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00148-3
• 作为产物：
  描述：

  methyl [2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4-O-methyl-β-D-glucopyranosid]uronate 在 palladium on activated charcoal 吡啶 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 methyl (2,3-di-O-benzoyl-4-O-methyl-α-D-gucopyranosyl trichloroacetamidate)uronate
  参考文献：
  名称：

  Syntheses of model compounds related to an antigenic epitope in pectic polysaccharides from Bupleurum falcatum L.

  摘要：

  Stereocontrolled syntheses of model compounds related to a category of the major antigenic epitope against anti-bupleurum 2IIc/PG-1-IgG from an anti-ulcer pectic polysaccharide are described. Glycosylation of the glucuronic acid donors methyl(2,3-di-O-benzoyl-4-O-methyl-alpha -D-glucopyranosyl trichloroacetimidate)uronate and methyl (2,3-di-O-benzoyl-4-O-methyl-beta -D-glucopyranosyl)uronate-(1 -->6)-2,3,4-tri-O-benzoyl-alpha -D-galactopyranosyl trichloroacetimidate with the common acceptor 2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-beta -D-galactopyranoside in the presence of trimethylsilyl triflate (TMSOTf) gave the desired di- and trisaccharide derivatives. Furthermore the products were transformed into the oligo-valent clustering saccharides, N,N',N"-tri-{5-[4-O-methyl-beta -D-glucopyranosyluronic acid-(1 --> 6)-beta -D-galactopyranosyloxy]pentylcarbonylaminoethyl}-1,3,5-benzenetriamide and N,N',N"-tri-{5-[4-O-methyl-beta -D-glucopyranosyluronic acid (1 --> 6)-beta -D-galactopyranosyl-(1 --> 6)-beta -D-galactopyranosyloxy]pentylcarbonylaminoethyl}-1,3,5-benzenetriamide. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00148-3

文献信息

• Syntheses of Model Compounds Related to an Antigenic Epitope in Pectic Polysaccharides from Bupleurum falcatum L. (II)
  作者：Yuhua Jin、Noriyasu Hada、Junko Oka、Osamu Kanie、Shusaku Daikoku、Yoshimi Kanie、Haruki Yamada、Tadahiro Takeda

  DOI：10.1248/cpb.54.485

  日期：——

  Stereocontrolled syntheses of model compounds related to a major antigenic epitope against antibupleurum 2IIc/PG-1-IgG from antiulcer pectic polysaccharide are described. A trisaccharide derivative (13) was prepared as a precursor and a novel and simple approach for the rational design of a glycocluster and glycodendrimer was developed, through the syntheses of the fluorescence-labeled glycocluster (2) and glycodendrimer (3).

  该研究描述了与抗溃疡果胶多糖中的一个主要抗原表位相关的模型化合物的立体控制合成。通过合成荧光标记的糖簇（2）和糖二聚体（3），制备了一种三糖衍生物（13）作为前体，并开发了一种合理设计糖簇和糖二聚体的新颖而简单的方法。
• Syntheses of model compounds related to an antigenic epitope in pectic polysaccharides from Bupleurum falcatum L.
  作者：Noriyasu Hada、Tomoko Ogino、Haruki Yamada、Tadahiro Takeda

  DOI：10.1016/s0008-6215(01)00148-3

  日期：2001.8

  Stereocontrolled syntheses of model compounds related to a category of the major antigenic epitope against anti-bupleurum 2IIc/PG-1-IgG from an anti-ulcer pectic polysaccharide are described. Glycosylation of the glucuronic acid donors methyl(2,3-di-O-benzoyl-4-O-methyl-alpha -D-glucopyranosyl trichloroacetimidate)uronate and methyl (2,3-di-O-benzoyl-4-O-methyl-beta -D-glucopyranosyl)uronate-(1 -->6)-2,3,4-tri-O-benzoyl-alpha -D-galactopyranosyl trichloroacetimidate with the common acceptor 2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-beta -D-galactopyranoside in the presence of trimethylsilyl triflate (TMSOTf) gave the desired di- and trisaccharide derivatives. Furthermore the products were transformed into the oligo-valent clustering saccharides, N,N',N"-tri-5-[4-O-methyl-beta -D-glucopyranosyluronic acid-(1 --> 6)-beta -D-galactopyranosyloxy]pentylcarbonylaminoethyl}-1,3,5-benzenetriamide and N,N',N"-tri-5-[4-O-methyl-beta -D-glucopyranosyluronic acid (1 --> 6)-beta -D-galactopyranosyl-(1 --> 6)-beta -D-galactopyranosyloxy]pentylcarbonylaminoethyl}-1,3,5-benzenetriamide. (C) 2001 Elsevier Science Ltd. All rights reserved.