8-(Methoxycarbonyl)octyl 2-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside | 143528-59-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 8-(Methoxycarbonyl)octyl 2-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: 8-methoxycarbonyloctyl (3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside；8-methoxycarbonyloctyl 2-O-(3,4,6-tri-O-benzyl-alpha-D-mannopyranosyl)-3,4,6-tri-O-benzyl-alpha-D-mannopyranoside；methyl 9-[(2S,3S,4S,5R,6R)-3-[(2R,3S,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxynonanoate
• CAS: 143528-59-0
• 化学式: C₆₄H₇₆O₁₃
• 分子量: 1053.3
• InChiKey: OVGPTHUENSISNL-CBNZHMTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  77
• 可旋转键数：
  33
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  8-(Methoxycarbonyl)octyl 2-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以94%的产率得到8-(Methoxycarbonyl)octyl 2-O-(α-D-mannopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of ω-(methoxycarbonyl)alkyl and 9-(methoxycarbonyl)-3,6-dioxanonyl glycopyranosides for the preparation of carbohydrate-protein conjugates

  摘要：

  Omega-(Methoxycarbonyl)alkyl glycopyranosides of D-mannose having C4, C-7, C-9, C-12, and C-15 carbon chains, L-fucose and 2-acetamido-2-deoxy-D-mannose having C-7 and C-9 carbon chains. D-xylose and 2-acetamido-2-deoxy-L-fucose having a C-9 carbon chian, and 9-(methoxycarbonyl)-3,6-dioxanoyl glycopyranosides of D-mannose. 2-acetamido-2-deoxy-D-mannose, and L-fucose were' synthesized as intermediates for coupling to human serum albumin in order to examine the effect of chain length and hydrophobicity of the spacer arm on the binding specificity of lectins. 8-(Methoxycarbonyl)octyl glycosides of beta-D-Man-(1 --> 2)-alpha-D-Man, alpha-D-Man-(1 --> 2)-alpha-D-Man, alpha-D-ManNAc-(1 --> 2)-alpha-D-Man, beta-D-GlcNAc-(1 --> 2)-alpha-D-Man, and their 6-O-positional isomers, beta-D-Man-(1 --> 6)-alpha-D-Man, alpha-D-Man-(1 --> 6)-alpha-D-Man, alpha-D-ManNAc-(1 --> 6)-alpha-D-Man, and beta-D-GlcNAc-(1 --> 6)-alpha-D-Man, were also synthesized.

  DOI：

  10.1016/s0008-6215(00)90517-2
• 作为产物：
  描述：

  油酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 sodium methylate 、 sodium 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 8-(Methoxycarbonyl)octyl 2-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthetic yeast oligomannosides as biological probes: α-d-Manp (1→3) α-d-Manp (1→2) α-d-Manp and α-d-Manp (1→3) α-d-Manp (1→2) α-d-Manp (1→2) α-d-Manp as Crohn's disease markers

  摘要：

  The anti-Saccharomyces cerevisiae antibodies (ASCA) are markers for Crohn's disease used for diagnostic, phenotypic characterization and sero-epidermiological studies. Antibody detection is made by different immunoenzymatic tests using S. cerevisiae mannans which are both complex and poorly standardized antigens. Here we construct the major discriminating epitopes comprised within this antigen. When coupled to linker arm and a peptidic carrier to functionalize microtiter plates, they were able to discriminate serological responses between Crohn's disease and ulcerative colitis, another form of inflammatory bowel disease. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.098

文献信息

• DENDRIMERS WITH A SACCHARIDE ENDING FOR ANTI-INFLAMMATORY PURPOSES
  申请人：Prandi Jacques

  公开号：US20130274210A1

  公开（公告）日：2013-10-17

  The present invention relates to dendrimers with a monosaccharide, oligosaccharide or polysaccharide terminal group, to their preparation method and their therapeutic uses, notably anti-inflammatory uses.

  本发明涉及具有单糖、寡糖或多糖末端基团的树状分子，其制备方法以及它们的治疗用途，特别是抗炎用途。
• Synthetic oligomannosides, preparation and uses thereof
  申请人：Centre Hospitalier Regional Universitaire (CHRU)

  公开号：US20030105060A1

  公开（公告）日：2003-06-05

  A pharmaceutical composition including a therapeutically effective amount of at least one oligomannoside produced by chemical synthesis which is homologous to a wall oligomannoside of an infectious organism or pathogen, or a derivative thereof, and a pharmaceutically acceptable vehicle.

  一种药物组合物，包括至少一种通过化学合成产生的与感染性生物或病原体的壁寡甘露聚糖同源的治疗有效量的寡甘露聚糖或其衍生物，以及一种药用可接受的载体。
• OLIGOMANNOSIDES DE SYNTHESE, LEUR PREPARATION ET LEURS UTILISATIONS
  申请人：CENTRE HOSPITALIER REGIONAL ET UNIVERSITAIRE DE LILLE

  公开号：EP1232167B1

  公开（公告）日：2010-05-05
• US7109182B2
  申请人：——

  公开号：US7109182B2

  公开（公告）日：2006-09-19
• Synthesis of ω-(methoxycarbonyl)alkyl and 9-(methoxycarbonyl)-3,6-dioxanonyl glycopyranosides for the preparation of carbohydrate-protein conjugates
  作者：Tamio Sugawara、Kunihiko Irie、Hiroyuki Iwasawa、Takayoshi Yoshikawa、Satoshi Okuno、Hiroshi K. Watanabe、Takashi Kato、Mitsuru Shibukawa、Yukio Ito

  DOI：10.1016/s0008-6215(00)90517-2

  日期：1992.6

  Omega-(Methoxycarbonyl)alkyl glycopyranosides of D-mannose having C4, C-7, C-9, C-12, and C-15 carbon chains, L-fucose and 2-acetamido-2-deoxy-D-mannose having C-7 and C-9 carbon chains. D-xylose and 2-acetamido-2-deoxy-L-fucose having a C-9 carbon chian, and 9-(methoxycarbonyl)-3,6-dioxanoyl glycopyranosides of D-mannose. 2-acetamido-2-deoxy-D-mannose, and L-fucose were' synthesized as intermediates for coupling to human serum albumin in order to examine the effect of chain length and hydrophobicity of the spacer arm on the binding specificity of lectins. 8-(Methoxycarbonyl)octyl glycosides of beta-D-Man-(1 --> 2)-alpha-D-Man, alpha-D-Man-(1 --> 2)-alpha-D-Man, alpha-D-ManNAc-(1 --> 2)-alpha-D-Man, beta-D-GlcNAc-(1 --> 2)-alpha-D-Man, and their 6-O-positional isomers, beta-D-Man-(1 --> 6)-alpha-D-Man, alpha-D-Man-(1 --> 6)-alpha-D-Man, alpha-D-ManNAc-(1 --> 6)-alpha-D-Man, and beta-D-GlcNAc-(1 --> 6)-alpha-D-Man, were also synthesized.