D-1,2,4,5-di-O-cyclohexylidene-3-((2'S,4'S,5'R)-3',4'-dimethyl-5'-phenyl-1',3',2'-oxazaphospholidin-2'-one)-myo-inositol | 193285-10-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: D-1,2,4,5-di-O-cyclohexylidene-3-((2'S,4'S,5'R)-3',4'-dimethyl-5'-phenyl-1',3',2'-oxazaphospholidin-2'-one)-myo-inositol
• 英文别名: D-1,2;4,5-di-O-cyclohexylidene-3-((2'S,4'S,5'R)-3',4'-dimethyl-5'-phenyl-1',3',2'-oxazaphospholidin-2'-one)-myo-inositol
• CAS: 193285-10-8
• 化学式: C₂₈H₄₀NO₈P
• 分子量: 549.601
• InChiKey: NLFBXCIASOLYOP-IVOVXCMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  38.0
• 可旋转键数：
  3.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  95.92
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  D-1,2,4,5-di-O-cyclohexylidene-3-((2'S,4'S,5'R)-3',4'-dimethyl-5'-phenyl-1',3',2'-oxazaphospholidin-2'-one)-myo-inositol 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 0.25h， 以97.9%的产率得到(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
• 作为产物：
  描述：

  (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one 、 1,2:4,5-dicyclohexylidene-myo-inositol 在 sodium hydride 作用下， 生成 D-1,2,4,5-di-O-cyclohexylidene-3-((2'S,4'S,5'R)-3',4'-dimethyl-5'-phenyl-1',3',2'-oxazaphospholidin-2'-one)-myo-inositol 、
  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