1,5-anhydro-2,3-dideoxy-3-diphenylphosphinoyl-D-ribo-hexitol | 639499-39-1

• 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: 1,5-anhydro-2,3-dideoxy-3-diphenylphosphinoyl-D-ribo-hexitol
• 英文别名: (2R,3R,4S)-4-diphenylphosphoryl-2-(hydroxymethyl)oxan-3-ol
• CAS: 639499-39-1
• 化学式: C₁₈H₂₁O₄P
• 分子量: 332.336
• InChiKey: DZIKBKBRBPDHHP-FGTMMUONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 1,5-anhydro-2,3-dideoxy-3-diphenylphosphinoyl-D-ribo-hexitol 在 咪唑 作用下， 以 乙二醇二甲醚 为溶剂， 反应 48.0h， 以75%的产率得到1,5-anhydro-2,3-dideoxy-6-O-tert-butyldimethylsilyl-3-diphenylphosphinoyl-D-ribo-hexitol
  参考文献：
  名称：

  Regioselective Synthesis of Phosphonylated Sugars from Reactions of Glycals with Diphenylphosphenium Cation

  摘要：

  Reaction of methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside 1 with two equivalents of diphertylphosphenium cation at 0degreesC gave the 1-phosphonylated 2-enopyranos ides 3alpha and 3beta as major products. Similarly, reaction of diphenylphosphenium cation with tri-O-acetylglycal afforded the same products in a similar ratio. In contrast, a reaction with tri-O-benzylglucal at reflux temperature of dichloromethane afforded the 3-phosphonylated sugar 13 as a major product. These reactions may proceed via stable allyl cations.

  DOI：

  10.1081/car-120025330
• 作为产物：
  描述：

  3,4,6-三苄氧基-D-葡萄烯糖 在 palladium on activated charcoal 三氯化铝 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、455.96 kPa 条件下， 反应 38.0h， 生成 1,5-anhydro-2,3-dideoxy-3-diphenylphosphinoyl-D-ribo-hexitol
  参考文献：
  名称：

  Regioselective Synthesis of Phosphonylated Sugars from Reactions of Glycals with Diphenylphosphenium Cation

  摘要：

  Reaction of methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside 1 with two equivalents of diphertylphosphenium cation at 0degreesC gave the 1-phosphonylated 2-enopyranos ides 3alpha and 3beta as major products. Similarly, reaction of diphenylphosphenium cation with tri-O-acetylglycal afforded the same products in a similar ratio. In contrast, a reaction with tri-O-benzylglucal at reflux temperature of dichloromethane afforded the 3-phosphonylated sugar 13 as a major product. These reactions may proceed via stable allyl cations.

  DOI：

  10.1081/car-120025330

文献信息

• Regioselective Synthesis of Phosphonylated Sugars from Reactions of Glycals with Diphenylphosphenium Cation
  作者：Akira Takano、Hiroyuki Fukuhara、Tadao Ohno、Masahiro Kutsuma、Tetsuya Fujimoto、Hirofusa Shirai、Ryozo Iriye、Akikazu Kakehi、Iwao Yamamoto

  DOI：10.1081/car-120025330

  日期：2003.1.10

  Reaction of methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside 1 with two equivalents of diphertylphosphenium cation at 0degreesC gave the 1-phosphonylated 2-enopyranos ides 3alpha and 3beta as major products. Similarly, reaction of diphenylphosphenium cation with tri-O-acetylglycal afforded the same products in a similar ratio. In contrast, a reaction with tri-O-benzylglucal at reflux temperature of dichloromethane afforded the 3-phosphonylated sugar 13 as a major product. These reactions may proceed via stable allyl cations.