8-methoxycarbonyloctyl β-D-galactofuranosyl-(1->3)-α-D-mannopyranoside | 109681-60-9

• 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 β-D-galactofuranosyl-(1->3)-α-D-mannopyranoside
• 英文别名: 8-methoxycarbonyloctyl-3-O-β-D-galactopyranosyl-α-D-mannopyranoside；methyl 9-[(2S,3S,4S,5R,6R)-4-[(2S,3R,4R,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynonanoate
• CAS: 109681-60-9
• 化学式: C₂₂H₄₀O₁₃
• 分子量: 512.552
• InChiKey: DMLWEIZOPDGMNN-LTOFVGMSSA-N

物化性质

• 沸点：
  755.8±60.0 °C(predicted)
• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  205
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  2,3,4,6-tetrakis-O-trimethylsilyl-α-D-mannopyranosyl iodide 在 甲醇 、 N-碘代丁二酰亚胺 、 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 四丁基碘化铵 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 23.75h， 生成 8-methoxycarbonyloctyl β-D-galactofuranosyl-(1->3)-α-D-mannopyranoside
  参考文献：
  名称：

  A NEW APPROACH TO A DISACCHARIDIC HAPTEN CONTAINING A GALACTOFURANOSYL ENTITY

  摘要：

  A short synthetic entry into the disaccharidic hapten beta-D-Galf-(1-->3)-alpha-D-Manp-O(CH2)(8)CO2Me containing a galactofuranosyl entity at the non-reducing part is described. The synthetic scheme was designed in such a way that each required building block could be obtained by minimizing the number of chemical and purification steps. Indeed, compound 8 was obtained according to a four step-one pot preparation.

  DOI：

  10.1081/car-100108662

文献信息

• 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。
• A NEW APPROACH TO A DISACCHARIDIC HAPTEN CONTAINING A GALACTOFURANOSYL ENTITY
  作者：Vincent Ferrières、Myriam Roussel、Muriel Gelin、Daniel Plusquellec

  DOI：10.1081/car-100108662

  日期：2001.12.31

  A short synthetic entry into the disaccharidic hapten beta-D-Galf-(1-->3)-alpha-D-Manp-O(CH2)(8)CO2Me containing a galactofuranosyl entity at the non-reducing part is described. The synthetic scheme was designed in such a way that each required building block could be obtained by minimizing the number of chemical and purification steps. Indeed, compound 8 was obtained according to a four step-one pot preparation.