2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1-> 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate | 743432-09-9

• 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: 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1-> 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate
• 英文别名: Bz(-2)[Bz(-3)][Bz(-5)]D-Araf(a1-2)[Bz(-3)][Bz(-4)][Bz(-6)]Man(a)-O-C(NH)CCl3；[(2R,3R,4S,5S,6R)-3,4-dibenzoyloxy-5-[(2R,3S,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)oxolan-2-yl]oxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl benzoate
• CAS: 743432-09-9
• 化学式: C₅₅H₄₄Cl₃NO₁₆
• 分子量: 1081.31
• InChiKey: OWPUKDJQLUITMC-FGYNHNKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  75
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  219
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1-> 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate 、 allyl 3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1-> 6)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-> 2)]-3,4-di-O-benzoyl-α-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以81.5%的产率得到allyl [2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1-> 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1-> 2)]-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1-> 6)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-> 2)]-3,4-di-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  Facile synthesis of arabinomannose penta- and decasaccharide fragments of the lipoarabinomannan of the equine pathogen, Rhodococcus equi

  摘要：

  Pentasaccharide repeating unit 20 of the lipoarabinomannan from the equine pathogen, Rhodococcus equi, and its dimer 31, were synthesized. The pentasaccharide was obtained by assembling a benzoylated 2,6-branched mannosyl trisaccharide acceptor 13 with a free hydroxyl group at C-2' of the mannose residue attached to the core mannose residue by (1 --> 6)-linkage, followed by coupling with 2,3,5-tri-O-benzoyl-alpha-D-arabinofuranosyl-(1 --> 2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (18), and by deacylation. Meanwhile, the decamer 31 was obtained by firstly preparing a benzoylated mannose (1 --> 6)-linked tetra-saccharide backbone 26 with 2-, 2"-O-ClAc, and 2'-, 2"'-O-Ac groups, respectively, then by dechloroacetylation and subsequent condensation with perbenzoylated trichloroacetimidate, and then by deacetylation and subsequent coupling with 18, and finally, by deacylation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.04.012
• 作为产物：
  描述：

  allyl 3,4,6-tri-O-benzoyl-α-D-mannopyranoside 在 palladium dichloride 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1-> 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Facile synthesis of arabinomannose penta- and decasaccharide fragments of the lipoarabinomannan of the equine pathogen, Rhodococcus equi

  摘要：

  Pentasaccharide repeating unit 20 of the lipoarabinomannan from the equine pathogen, Rhodococcus equi, and its dimer 31, were synthesized. The pentasaccharide was obtained by assembling a benzoylated 2,6-branched mannosyl trisaccharide acceptor 13 with a free hydroxyl group at C-2' of the mannose residue attached to the core mannose residue by (1 --> 6)-linkage, followed by coupling with 2,3,5-tri-O-benzoyl-alpha-D-arabinofuranosyl-(1 --> 2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (18), and by deacylation. Meanwhile, the decamer 31 was obtained by firstly preparing a benzoylated mannose (1 --> 6)-linked tetra-saccharide backbone 26 with 2-, 2"-O-ClAc, and 2'-, 2"'-O-Ac groups, respectively, then by dechloroacetylation and subsequent condensation with perbenzoylated trichloroacetimidate, and then by deacetylation and subsequent coupling with 18, and finally, by deacylation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.04.012

文献信息

• Facile synthesis of arabinomannose penta- and decasaccharide fragments of the lipoarabinomannan of the equine pathogen, Rhodococcus equi
  作者：Zuchao Ma、Jianjun Zhang、Fanzuo Kong

  DOI：10.1016/j.carres.2004.04.012

  日期：2004.7

  Pentasaccharide repeating unit 20 of the lipoarabinomannan from the equine pathogen, Rhodococcus equi, and its dimer 31, were synthesized. The pentasaccharide was obtained by assembling a benzoylated 2,6-branched mannosyl trisaccharide acceptor 13 with a free hydroxyl group at C-2' of the mannose residue attached to the core mannose residue by (1 --> 6)-linkage, followed by coupling with 2,3,5-tri-O-benzoyl-alpha-D-arabinofuranosyl-(1 --> 2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (18), and by deacylation. Meanwhile, the decamer 31 was obtained by firstly preparing a benzoylated mannose (1 --> 6)-linked tetra-saccharide backbone 26 with 2-, 2"-O-ClAc, and 2'-, 2"'-O-Ac groups, respectively, then by dechloroacetylation and subsequent condensation with perbenzoylated trichloroacetimidate, and then by deacetylation and subsequent coupling with 18, and finally, by deacylation. (C) 2004 Elsevier Ltd. All rights reserved.