D-1,2-O-(L-1,7,7-trimethyl<2.2.1>bicyclohept-2-ylidene)-myo-inositol | 143617-31-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: D-1,2-O-(L-1,7,7-trimethyl<2.2.1>bicyclohept-2-ylidene)-myo-inositol
• 英文别名: 1,2-O-(L-1,7,7-trimethyl[2.2.1]bicyclohept-6-ylidene)-D-myo-inositol；(1S,2R,3R,4S,5S,6R,7S,8S,11S)-myo-inositol-1,2-camphor acetal；(1R,2S,3S,4R,5S,6R)-5,6-[(1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,2-diyldioxy]cyclohexane-1,2,3,4-tetrol；D-1,2-O-(L-1,7,7-trimethyl[2.2.1]bicyclohept-2-ylidene)-myo-inositol
• CAS: 143617-31-6
• 化学式: C₁₆H₂₆O₆
• 分子量: 314.379
• InChiKey: RGNPNZRZAPXKMY-QLAUEBBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.23
• 重原子数：
  22.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.38
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  D-1,2-O-(L-1,7,7-trimethyl<2.2.1>bicyclohept-2-ylidene)-myo-inositol 在 4 A molecular sieve 、 sodium hydride 、 N,N-二异丙基乙胺 、 三氟甲烷磺酸甲酯 作用下， 以 1,4-二氧六环 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.0h， 生成
  参考文献：
  名称：

  Efficient routes to glucosamine-myo-inositol derivatives, key building blocks in the synthesis of glycosylphosphatidylinositol anchor substances

  摘要：

  Short synthetic routes to protected derivatives of 2-amino-2-deoxy-alpha-D-glucopyranosyl-(1-->6)-D-myo-inositol are described. Various 2-azido-2-deoxy-glucosyl donors were synthesized, starting front, D-Glucal or glucosamine hydrochloride. Derivatives of 1,2- and 2,3-D-myo-inositol-camphanylidene acetals were prepared to function as glycosyl acceptors. The subsequent glycosylations produced useful building blocks for the synthesis of GPI-anchor substances. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01241-8
• 作为产物：
  描述：

  左旋樟脑 在 硫酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 51.0h， 生成 D-1,2-O-(L-1,7,7-trimethyl<2.2.1>bicyclohept-2-ylidene)-myo-inositol
  参考文献：
  名称：

  Efficient routes to glucosamine-myo-inositol derivatives, key building blocks in the synthesis of glycosylphosphatidylinositol anchor substances

  摘要：

  Short synthetic routes to protected derivatives of 2-amino-2-deoxy-alpha-D-glucopyranosyl-(1-->6)-D-myo-inositol are described. Various 2-azido-2-deoxy-glucosyl donors were synthesized, starting front, D-Glucal or glucosamine hydrochloride. Derivatives of 1,2- and 2,3-D-myo-inositol-camphanylidene acetals were prepared to function as glycosyl acceptors. The subsequent glycosylations produced useful building blocks for the synthesis of GPI-anchor substances. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01241-8

文献信息

• The synthesis of homochiral inositol phosphates from myo-inositol
  作者：K.Michał Pietrusiewicz、Grzegorz M. Salamończyk、Karol S. Bruzik、Wanda Wieczorek

  DOI：10.1016/s0040-4020(01)88305-8

  日期：1992.1

  conversion of myo-inositol into homochiral inositol phosphates is presented, and is illustrated with total synthesis of myo-inositol 1-phosphate, 2-deoxy-myo-inositol 1-phosphate, myo-inositol 3-phosphate, myo-inositol 4-phosphate, myo-inositol 1,4-bisphosphate, myo-inositol 1,4,5-trisphosphate, and myo-inositol 3,4,5,6-tetrakisphosphate. The syntheses start with selfresolving myo-inositol camphanylidene

  高效转换的一个新的合成方法肌醇肌醇成纯手性肌醇磷酸被呈现，并且与全合成所示肌醇-1-磷酸，2-脱氧肌醇-1-磷酸，肌醇肌醇-3-磷酸，肌肌醇-4-磷酸，肌醇肌醇1,4-二磷酸，肌醇肌醇1,4,5-三磷酸和肌醇肌醇3,4,5,6-四磷酸盐。该合成开始selfresolving肌肌醇camphanylidene顺-monoacetals 2A和2A'分别从母体环糖醇和D-和L-樟脑二甲基缩醛一步获得，并通过沉淀驱动的平衡方便地收获。合成的关键步骤是2a和2a'的选择性单磷酸化，选择性双甲硅烷基化和选择性三酰基化，以及使用二氯磷酸二苄酯和2-二甲氨基-5,6-苯并-1,3,2-二氧杂磷杂环戊烷来实现单磷酸化和多磷酸化。为了支持立体化学分配，还提出了一种中间体完全保护的肌醇衍生物之一的X射线结构。