L-1-O-benzyl-5,6-O-cyclohexylidene-3-deoxy-chiro-inositol | 161104-10-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: L-1-O-benzyl-5,6-O-cyclohexylidene-3-deoxy-chiro-inositol
• 英文别名: (3aS,4R,6S,7S,7aR)-7-phenylmethoxyspiro[3a,4,5,6,7,7a-hexahydro-1,3-benzodioxole-2,1'-cyclohexane]-4,6-diol
• CAS: 161104-10-5
• 化学式: C₁₉H₂₆O₅
• 分子量: 334.412
• InChiKey: MORPIEPGKNRPKN-FLXSYLCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  L-1-O-benzyl-5,6-O-cyclohexylidene-3-deoxy-chiro-inositol 在 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 26.0h， 生成 L-2,4,5-tri-O-benzoyl-1-O-benzyl-3-deoxy-chiro-inositol
  参考文献：
  名称：

  Stereoselective synthesis of 6-deoxy and 3,6-dideoxy-D-myo-inositol precursors of deoxy-myo-inositol phosphate analogues from D-galactose

  摘要：

  The synthesis of chiral protected D-6-deoxy-myo-inositol derivatives from D-galactose is described. Ferrier rearrangement of hexenogalactopyranosides has been employed to produce the corresponding 6-deoxy-cyclohexanone polyols. The stereoselectivity of the carbocyclic transformation was discussed on the basis of the experimental data and a mechanism has been proposed. From deoxy-inososes, the access to a variety of 6-deoxy and 3,6-dideoxy-myo-inositol was performed to prepare suitable monool, diol and triol precursors for the synthesis of D-deoxy-myo-inositol phosphate analogues. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10101-6
• 作为产物：
  描述：

  methyl 6-chloro-3,4-O-cyclohexylidene-6-deoxy-β-D-galactopyranoside 在 氢氧化钾 、 sodium tetrahydroborate 、 cerium(III) chloride 、 苄基三甲基氯化铵 、 sodium hydride 、 硫脲 、 mercury dichloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 L-1-O-benzyl-5,6-O-cyclohexylidene-3-deoxy-chiro-inositol
  参考文献：
  名称：

  Stereoselective synthesis of 6-deoxy and 3,6-dideoxy-D-myo-inositol precursors of deoxy-myo-inositol phosphate analogues from D-galactose

  摘要：

  The synthesis of chiral protected D-6-deoxy-myo-inositol derivatives from D-galactose is described. Ferrier rearrangement of hexenogalactopyranosides has been employed to produce the corresponding 6-deoxy-cyclohexanone polyols. The stereoselectivity of the carbocyclic transformation was discussed on the basis of the experimental data and a mechanism has been proposed. From deoxy-inososes, the access to a variety of 6-deoxy and 3,6-dideoxy-myo-inositol was performed to prepare suitable monool, diol and triol precursors for the synthesis of D-deoxy-myo-inositol phosphate analogues. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10101-6

文献信息

• Stereoselective synthesis of inositol mono, bis and trisphosphate analogues from 6-deoxy- d -inositol precursors
  作者：Mauro Vieira de Almeida、Didier Dubreuil、Jeannine Cleophax、Catherine Verre-Sebrié、Muriel Pipelier、Guillaume Prestat、Georges Vass、Stéphane D Gero

  DOI：10.1016/s0040-4020(99)00365-8

  日期：1999.6

  The synthesis of opticaly pure deoxy-myo-inositol mono, bis and trisphosphate analogues is described from 4-O-benzyl-2,3-di-O-cyclohexylidene-6-deoxy-myo-inositol and corresponding 1,5 epimer chiro-inositol. These precursors, which derive from galactose, are used to accede to a variety of cyclitol intermediates employing protection/deprotection sequence. The phosphorylation procedure was performed to produce free and original substituted phosphate derivatives aimed to be incorporated through the lipidic cell membrane for in vivo evaluation. (C) 1999 Elsevier Science Ltd. All rights reserved.