2,3:4,6-di-O-cyclohexylidene-α-D-mannopyranosyl chloride | 70835-79-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 2,3:4,6-di-O-cyclohexylidene-α-D-mannopyranosyl chloride
• CAS: 70835-79-9
• 化学式: C₁₈H₂₇ClO₅
• 分子量: 358.862
• InChiKey: VMAMNENGNGFBRA-OWYFMNJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  24.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,3:4,6-di-O-cyclohexylidene-α-D-mannopyranosyl chloride 在 4 A molecular sieve 、 水 、 sodium methylate 、 silver carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 72.25h， 生成 6-O-β-D-mannopyranosyl-D-glucose
  参考文献：
  名称：

  Garegg, Per J.; Iversen, Tommy; Johansson, Rolf, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1980, vol. 34, # 7, p. 505 - 508

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3:4,6-di-O-cyclohexylidene-α-D-mannopyranose 在 甲基磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以83%的产率得到2,3:4,6-di-O-cyclohexylidene-α-D-mannopyranosyl chloride
  参考文献：
  名称：

  Garegg, Per J.; Iversen, Tommy; Johansson, Rolf, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1980, vol. 34, # 7, p. 505 - 508

  摘要：

  DOI：

文献信息

• Enantioselective complexation of carbohydrate or crown ether hosts with organic ammonium ion guests detected by FAB mass spectrometry
  作者：Masami Sawada、Yasuo Okumura、Motohiro Shizuma、Yoshio Takai、Yukio Hidaka、Hitoshi Yamada、Takanori Tanaka、Takahiro Kaneda、Keiji Hirose

  DOI：10.1021/ja00069a041

  日期：1993.8

  Enantioselective host-guest complexation has been demonstrated by FAB mass spectrometry. Among several carbohydrates, a modified beta-mannofuranoside 6b as well as chiral crown ethers 10 and 13, differentiates a chiral ammonium ion guest such as the (1-(1-naphthyl)ethyl)ammonium ion. The relative peak intensity (RPI) method has been applied to the evaluation of such diastereomcric complex ions where the peak intensity of the target host (M)-guest (A+) complex ion I((M+A)+) is compared to that of the internal standard host (R)-guest (A+) ion I((R+A)+): the RPI value = I((M+A)+)/I((R+A)+). The present enantioselectivity is characterized by the RPI ratio value I((M+A(R))+)/I((M+A(s))+) in the range 1.2-1.6 (1.0 +/- 0.1 nonenantioselectivity). The observed preference of the (R)-enantiomer guest is compatible with model examinations and related coloration results. With chiral crown ether 13, a close correspondence exists between the FABMS/RPI enantioselection and that of strictly related solution-phase energetics in association equilibria. The usefulness of the RPI method is also shown by comparison to the relevant equilibrium constants (NMR titration) in solution.
• Garegg, Per J.; Johansson, Rolf; Samuelsson, Bertil, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1981, vol. 35, # 9, p. 635 - 636
  作者：Garegg, Per J.、Johansson, Rolf、Samuelsson, Bertil

  DOI：——

  日期：——