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 | 372518-32-6

• 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: 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
• 英文别名: methyl (2S,3S,4S,5R,6R)-4,5-dibenzoyloxy-3-methoxy-6-[[(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methoxy]oxane-2-carboxylate
• CAS: 372518-32-6
• 化学式: C₅₁H₄₄Cl₃NO₁₇
• 分子量: 1049.27
• InChiKey: DZKPBPGJQRJAHE-OMVLYEBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  72
• 可旋转键数：
  23
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  228
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  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 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 5-[2-aminoethyleneaminocarbonyl]pentyl [methyl (2,3-di-O-benzoyl-4-O-methyl-β-D-glucopyranosyl)uronate]-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
  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 、 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 19.5h， 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

文献信息

• 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.