8-methoxycarbonyloctyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside | 109681-57-4

• 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-methoxycarbonyloctyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: methyl 9-[(2S,3S,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxynonanoate
• CAS: 109681-57-4
• 化学式: C₃₇H₄₈O₈
• 分子量: 620.783
• InChiKey: CPJJUFZBBBEBOO-YBEDYFLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  45
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  8-methoxycarbonyloctyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 8-(methoxycarbonyl)octyl 2-O-(α-D-arabinofuranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of Oligosaccharide Fragments of the Lipoarabinomannan from Rhodococcus ruber *

  摘要：

  The synthesis of two oligosaccharide fragments (I and 2) of the lipoarabinomannan from Rhodococcus ruber is reported. Thioglycoside donors were used to assemble these glycans, which were prepared as their 8-(methoxycarbonyl)octyl glycosides for potential incorporation into neoglycoconjugates.

  DOI：

  10.1081/car-200067114
• 作为产物：
  描述：

  油酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸 、 sodium methylate 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 8-methoxycarbonyloctyl 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。
• Preparation of 8-methoxycarbonyloctyl glycosides of α-d-mannopyranose, 2-O-α-mannopyranosyl-α-d-mannopyranose, β-d-galactofuranose, and 3-O-β-d-galactofuranosyl-α-d-mannopyranose
  作者：David S. Tsui、Philip A.J. Gorin

  DOI：10.1016/s0008-6215(00)90094-6

  日期：1986.11

  with the general structure mono-(or di-)saccharide-lipid spacer-protein having possible antigenic and immunogenic activity in respect to infection with Trypanosoma cruzi. Tri-O-acetyl-1,2-O-(1-methoxyethylidene) derivatives of D-mannopyranose and D-galactofuranose were treated with alcohols in the presence and absence of mercuric bromide to give orthoesters which rearranged into glycosides.

  制备了α-D-甘露吡喃糖，2-O-α-甘露吡喃糖基-α-D-甘露吡喃糖，β-D-半乳糖呋喃糖和3-O-β-D-半乳糖呋喃糖基α-D-甘露吡喃糖的8-甲氧羰基辛基糖苷。作为合成具有一般结构的复合物的中间体，单（或二）糖-脂质间隔蛋白对克鲁斯锥虫的感染具有可能的抗原和免疫原活性。在存在和不存在溴化汞的情况下，用醇处理D-甘露吡喃糖和D-半乳糖呋喃糖的三-O-乙酰基-1,2-O-（1-甲氧基亚乙基）衍生物，得到原酸酯，其重新排列成糖苷。
• 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.
• Vandana; Hindsgaul, Ole; Baenziger, Jaques, Canadian Journal of Chemistry, 1987, vol. 65, p. 1645 - 1652
  作者：Vandana、Hindsgaul, Ole、Baenziger, Jaques

  DOI：——

  日期：——
• HINDSGAUL, VANDANA;HINDSGAUL, OLE;BAENZIGER, JACQUES U., CAN. J. CHEM., 65,(1987) N 7, 1645-1642
  作者：HINDSGAUL, VANDANA、HINDSGAUL, OLE、BAENZIGER, JACQUES U.

  DOI：——

  日期：——