n-decyl β-D-mannofuranoside | 111549-68-9

• 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: n-decyl β-D-mannofuranoside
• 英文别名: (2R,3S,4R,5R)-2-decoxy-5-[(1R)-1,2-dihydroxyethyl]oxolane-3,4-diol
• CAS: 111549-68-9
• 化学式: C₁₆H₃₂O₆
• 分子量: 320.426
• InChiKey: CLMTYVFXJOTEDJ-IBEHDNSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  癸醇 、 2,3:5,6-di-O-ethyl-boranediyl-α-D-mannofuranosylbromide 生成 n-decyl β-D-mannofuranoside
  参考文献：
  名称：

  Amphiphilic Carbohydrate-Based Mesogens; I. MesognicO-n-Alkyl β-D-Mannofuranosides: Synthesis of a Novel Homologous Series of Glycosides

  摘要：

  通过对 2,3; 5,6-di-O-ethylboranediyl-α-D-mannofuranosyl bromide 进行糖基化，并对受保护的糖苷进行脱芳基反应，立体选择性地制备出新的中生 O-n- 烷基δ-D-mannofuranosides，且收率良好。

  DOI：

  10.1055/s-1987-27945

文献信息

• A convenient synthesis of alkyl d-glycofuranosiduronic acids and alkyl d-glycofuranosides from unprotected carbohydrates
  作者：Vincent Ferrières、Jean-Noël Bertho、Daniel Plusquellec

  DOI：10.1016/s0008-6215(98)00197-9

  日期：1998.9

  O-Glycosylation of a variety of long chain alcohols with totally unprotected uronic acids (D-glucuronic and D-galacturonic acids) and neutral carbohydrates (D-glucose, D-galactose, D-mannose and D-glucofuranurono-6,3-lactone), performed in heterogeneous media and promoted by Lewis acids (ferric chloride or boron trifluoride diethyl etherate), afforded alkyl D-glycofuranosiduronic acids and alkyl D-glycofuranosides, respectively, in high yields. Both chemoselectivity and anomeric stereoselectivity were enhanced by complexing agents, i.e. calcium or barium chloride. (C) 1998 Elsevier Science Ltd. All rights reserved