(3R,4S,5R)-3,4,6-tris(benzyloxy)-2-methylenehexane-1,5-diol | 1265884-07-8

• 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: (3R,4S,5R)-3,4,6-tris(benzyloxy)-2-methylenehexane-1,5-diol
• 英文别名: (3R,4S,5R)-3,4,6-tris(benzyloxy)-5-hydroxy-2-hydroxymethylhex-1-ene；(3R,4S,5R)-2-methylidene-3,4,6-tris(phenylmethoxy)hexane-1,5-diol
• CAS: 1265884-07-8
• 化学式: C₂₈H₃₂O₅
• 分子量: 448.559
• InChiKey: FTDZCYKCCKTHCX-FCEKVYKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R)-3,4,6-tris(benzyloxy)-2-methylenehexane-1,5-diol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (2S,3S,4R)-1-(2'-hydroxyethyl)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-C-methylene-piperidine
  参考文献：
  名称：

  InCl3–CH3CN–H2O: an efficient catalyst-solvent combination for the synthesis of Perlin aldehydes and related compounds. Application in the synthesis of unnatural l-azasugars

  摘要：

  InCl3-CH3CN-H2O has been found to be an efficient catalyst-solvent combination for the synthesis of Perlin aldehydes and related compounds. While acetylated glycals afforded the Perlin aldehydes directly with InCl3 and water, benzylated glycals on the other hand provided the hemiacetals under identical condition. The methodology reports a non-mercurial approach to Perlin aldehydes. Noteworthy is that this reaction is more facile as well as highly selective with glycals possessing a hydroxyl as a leaving group than with a benzyloxy group. Extension of this reaction to 2-C-hydroxymethyl glycals resulted in the formation of the corresponding hemiacetals, which were further transformed in to unsaturated azasugars with an exo-methylene group at C-2 position. Glycosidase inhibition studies reveal that these compounds display selectivity in inhibiting glucosidases rather than galactosidases. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.050
• 作为产物：
  描述：

  1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-lyxo-hex-1-enitol 在 indium(III) chloride 、 水 、 sodium tetrahydroborate 作用下， 以 乙腈 、 甲醇 为溶剂， 反应 4.5h， 以0.179 g的产率得到(3R,4S,5R)-3,4,6-tris(benzyloxy)-2-methylenehexane-1,5-diol
  参考文献：
  名称：

  InCl3–CH3CN–H2O: an efficient catalyst-solvent combination for the synthesis of Perlin aldehydes and related compounds. Application in the synthesis of unnatural l-azasugars

  摘要：

  InCl3-CH3CN-H2O has been found to be an efficient catalyst-solvent combination for the synthesis of Perlin aldehydes and related compounds. While acetylated glycals afforded the Perlin aldehydes directly with InCl3 and water, benzylated glycals on the other hand provided the hemiacetals under identical condition. The methodology reports a non-mercurial approach to Perlin aldehydes. Noteworthy is that this reaction is more facile as well as highly selective with glycals possessing a hydroxyl as a leaving group than with a benzyloxy group. Extension of this reaction to 2-C-hydroxymethyl glycals resulted in the formation of the corresponding hemiacetals, which were further transformed in to unsaturated azasugars with an exo-methylene group at C-2 position. Glycosidase inhibition studies reveal that these compounds display selectivity in inhibiting glucosidases rather than galactosidases. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.050

文献信息

• Synthesis of C2-Methylene Glycitols from 1,2-Cyclopropanated Sugars: En Route to Iminosugar Analogues
  作者：Perali Sridhar、Kalapati Seshadri

  DOI：10.1055/s-0033-1340617

  日期：——

  borohydride. The generality of the methodology was evaluated by applying it to a series of 1,2-cyclopropanated pyranoses as well as furanoses to give the corresponding C2-methylene glycitol derivatives. Furthermore, the obtained glycitols were converted into 1-deoxy-C2-methylene iminosugar derivatives. C2-Methylene glycitols were synthesized in three steps by halonium ion mediated solvolytic ring opening

  摘要 通过卤离子介导的1,2-环丙烷化糖的溶剂化开环，使用碳酸钾在乙腈水溶液中的脱卤化氢以及用硼氢化钠还原，可通过三步合成C2-亚甲基糖醇。该方法的一般性通过将其应用于一系列1,2-环丙烷化的吡喃糖酶和呋喃糖酶进行评估，以得到相应的C2-亚甲基糖醇衍生物。此外，将获得的糖醇转化为1-脱氧-C 2-亚甲基亚氨基糖衍生物。 通过卤离子介导的1,2-环丙烷化糖的溶剂化开环，使用碳酸钾在乙腈水溶液中的脱卤化氢以及用硼氢化钠还原，可通过三步合成C2-亚甲基糖醇。该方法的一般性通过将其应用于一系列1,2-环丙烷化的吡喃糖酶和呋喃糖酶进行评估，以得到相应的C2-亚甲基糖醇衍生物。此外，将获得的糖醇转化为1-脱氧-C 2-亚甲基亚氨基糖衍生物。
• InCl3–CH3CN–H2O: an efficient catalyst-solvent combination for the synthesis of Perlin aldehydes and related compounds. Application in the synthesis of unnatural l-azasugars
  作者：Paramathevar Nagaraj、Muthupandian Ganesan、Namakkal G. Ramesh

  DOI：10.1016/j.tet.2010.11.050

  日期：2011.1

  InCl3-CH3CN-H2O has been found to be an efficient catalyst-solvent combination for the synthesis of Perlin aldehydes and related compounds. While acetylated glycals afforded the Perlin aldehydes directly with InCl3 and water, benzylated glycals on the other hand provided the hemiacetals under identical condition. The methodology reports a non-mercurial approach to Perlin aldehydes. Noteworthy is that this reaction is more facile as well as highly selective with glycals possessing a hydroxyl as a leaving group than with a benzyloxy group. Extension of this reaction to 2-C-hydroxymethyl glycals resulted in the formation of the corresponding hemiacetals, which were further transformed in to unsaturated azasugars with an exo-methylene group at C-2 position. Glycosidase inhibition studies reveal that these compounds display selectivity in inhibiting glucosidases rather than galactosidases. (C) 2010 Elsevier Ltd. All rights reserved.