8-methoxycarbonyloctyl β-D-galactofuranoside | 109681-55-2

• 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-galactofuranoside
• 英文别名: methyl 9-[(2R,3R,4R,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxynonanoate
• CAS: 109681-55-2
• 化学式: C₁₆H₃₀O₈
• 分子量: 350.409
• InChiKey: HYUKRGWXBFAMMS-CSOUEMRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  8-乙氧羰基辛醇 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 8-methoxycarbonyloctyl β-D-galactofuranoside
  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。