D-4-O-benzyl-2,3-O-cyclohexylidene-6-deoxy-myo-1-inosose | 156712-77-5

• 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: D-4-O-benzyl-2,3-O-cyclohexylidene-6-deoxy-myo-1-inosose
• CAS: 156712-77-5
• 化学式: C₁₉H₂₄O₅
• 分子量: 332.397
• InChiKey: GREJPBKWGASYSC-LAVFITLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 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：
  0.63
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  D-4-O-benzyl-2,3-O-cyclohexylidene-6-deoxy-myo-1-inosose 在 palladium on activated charcoal 锂硼氢 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， -40.0~25.0 ℃ 、34.48 kPa 条件下， 反应 13.0h， 生成 (1R,2S,4S,5S)-cyclohexane-1,2,3,4,5-pentol
  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：

  在 偶氮二甲酸二异丙酯 、 硫脲 、 三苯基膦 、 苯甲酸 、 mercury dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 4.33h， 生成 D-4-O-benzyl-2,3-O-cyclohexylidene-6-deoxy-myo-1-inosose
  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

• Synthesis of deoxy phosphatidylinositol analogues and phosphonate isosters of Ins(1,4,5)P3
  作者：Mauro Vieira de Almeida、Jeannine Cleophax、Alice Gateau-Olesker、Guillaume Prestat、Didier Dubreuil、Stéphane D Gero

  DOI：10.1016/s0040-4020(99)00793-0

  日期：1999.11

  The synthesis of phosphatidylinositol analogues, 6-deoxy Ins 1-(1,2-di-O-palmitoyl-sn-glycero)phosphate and 4,5-bisphosphate derivatives is presented. Two series of phosphonate isosters, 6-deoxy Ins(1)-butylphosphonate and 6-deoxy Ins(1)-C-methylenephosphonate as well as its 4,5-bisphosphate analogue were also prepared. All phosphoinositide analogues were obtained from cyclohexanone polyol derived

  提出了磷脂酰肌醇类似物，6-脱氧Ins 1-（1,2-二-O-棕榈酰基-sn-甘油）磷酸酯和4,5-双磷酸酯衍生物的合成。-两个系列膦酸酯等排物的，6-脱氧项（1）和-butylphosphonate 6-脱氧项（1）ç还制备-methylenephosphonate以及其4,5-二磷酸类似物。所有磷酸肌醇类似物均获自衍生自d-半乳糖的环己酮多元醇。在PtdIns和InsP衍生物的1位上改变电荷分布，通过用烷基取代基或PC键取代POH基团，可抵抗脂肪酶的裂解，可以在酶的进一步策略性酶水平上抑制活性。肌苷级联。