(1R,2S)-2-(methylamino)-1-phenylpropyl ((1R,2S,3R,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl) hydrogen phosphate | 193285-11-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S)-2-(methylamino)-1-phenylpropyl ((1R,2S,3R,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl) hydrogen phosphate
• CAS: 193285-11-9
• 化学式: C₁₆H₂₆NO₉P
• 分子量: 407.357
• InChiKey: FWECCZDKCBTCGU-YHSBAUHPSA-N

物化性质

• 沸点：
  582.8±60.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.34
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  168.94
• 氢给体数：
  7.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-(methylamino)-1-phenylpropyl ((1R,2S,3R,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl) hydrogen phosphate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、344.73 kPa 条件下， 反应 16.0h， 生成 D-MYO-肌醇3-磷酸酯
  参考文献：
  名称：

  Structure of (±)-1,2;4,5-di-O-cyclohexylidene myo-inositol and synthesis of myo-inositol 3-phosphate via its phosphorylation with (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one

  摘要：

  The crystal structure of (+/-)-1,2;4,5-di-O-cyclohexylidene myo-inositol, refined to R=2.9%, shows interestingly disordered (flip-flop) hydrogen bonding. The higher reactivity of the 1/3 positions (rather than 4/6) has been evaluated using semi-empirical calculations. This diol has been phosphorylated with (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one and the diastereoisomer derived from phosphorylation at the 3-position was isolated by crystallisation, Deprotection with TFA/H2O then H-2/Pd-C afforded myo-inositol 3-phosphate in only four steps from myo-inositol. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00109-2
• 作为产物：
  描述：

  1,2:4,5-dicyclohexylidene-myo-inositol 在 sodium hydride 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 3.25h， 生成 (1R,2S)-2-(methylamino)-1-phenylpropyl ((1R,2S,3R,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl) hydrogen phosphate
  参考文献：
  名称：

  Structure of (±)-1,2;4,5-di-O-cyclohexylidene myo-inositol and synthesis of myo-inositol 3-phosphate via its phosphorylation with (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one

  摘要：

  The crystal structure of (+/-)-1,2;4,5-di-O-cyclohexylidene myo-inositol, refined to R=2.9%, shows interestingly disordered (flip-flop) hydrogen bonding. The higher reactivity of the 1/3 positions (rather than 4/6) has been evaluated using semi-empirical calculations. This diol has been phosphorylated with (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one and the diastereoisomer derived from phosphorylation at the 3-position was isolated by crystallisation, Deprotection with TFA/H2O then H-2/Pd-C afforded myo-inositol 3-phosphate in only four steps from myo-inositol. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00109-2

文献信息

• Structure of (±)-1,2;4,5-di-O-cyclohexylidene myo-inositol and synthesis of myo-inositol 3-phosphate via its phosphorylation with (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one
  作者：Ian D. Spiers、Carl H. Schwalbe、Alexander J. Blake、Kevin R.H. Solomons、Sally Freeman

  DOI：10.1016/s0008-6215(97)00109-2

  日期：1997.7

  The crystal structure of (+/-)-1,2;4,5-di-O-cyclohexylidene myo-inositol, refined to R=2.9%, shows interestingly disordered (flip-flop) hydrogen bonding. The higher reactivity of the 1/3 positions (rather than 4/6) has been evaluated using semi-empirical calculations. This diol has been phosphorylated with (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one and the diastereoisomer derived from phosphorylation at the 3-position was isolated by crystallisation, Deprotection with TFA/H2O then H-2/Pd-C afforded myo-inositol 3-phosphate in only four steps from myo-inositol. (C) 1997 Elsevier Science Ltd.