(4S,5S)-4-(2-pyridyl)-5-<(tert-butyldiphenylsilyl)oxy>methyl-2,2-dimethyl-1,3-dioxolane | 156145-70-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5S)-4-(2-pyridyl)-5-<(tert-butyldiphenylsilyl)oxy>methyl-2,2-dimethyl-1,3-dioxolane
• CAS: 156145-70-9
• 化学式: C₂₇H₃₃NO₃Si
• 分子量: 447.649
• InChiKey: UNPJTYGFWUIXMA-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  40.58
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-(2-pyridyl)-5-<(tert-butyldiphenylsilyl)oxy>methyl-2,2-dimethyl-1,3-dioxolane 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 双氧水 、 sodium 、 氢化钾 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 (4S,5R)-4-(2-pyridyl)-5-(diphenylphosphino)methyl-2,2-dimethyl-1,3-dioxolane P-oxide
  参考文献：
  名称：

  Synthesis of homochiral pyridyl, bipyridyl and phosphino derivatives of 2,2-dimethyl-1,3-dioxolane: Use in asymmetric catalysis

  摘要：

  Homochiral pyridyl, bipyridyl and phosphino derivatives of 2,2-dimethyl-1,3-dioxolane were prepared from L-(+)-tartrate. These compounds were assessed in metal catalyzed asymmetric addition of diethylzinc to benzaldehyde, hydroformylation of styrene, hydrocarboethoxylation of styrene and allylic alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00086-9
• 作为产物：
  描述：

  4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threose oxime 在 decamethylrhenocene 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 120.0 ℃ 、1.42 MPa 条件下， 反应 25.0h， 生成 (4S,5S)-4-(2-pyridyl)-5-<(tert-butyldiphenylsilyl)oxy>methyl-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Synthesis of homochiral pyridyl, bipyridyl and phosphino derivatives of 2,2-dimethyl-1,3-dioxolane: Use in asymmetric catalysis

  摘要：

  Homochiral pyridyl, bipyridyl and phosphino derivatives of 2,2-dimethyl-1,3-dioxolane were prepared from L-(+)-tartrate. These compounds were assessed in metal catalyzed asymmetric addition of diethylzinc to benzaldehyde, hydroformylation of styrene, hydrocarboethoxylation of styrene and allylic alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00086-9

文献信息

• (−)-(4S,5R)-4-(2-pyridyl)-5-(diphenylphosphino)methyl-2,2-dimethyl-1,3-dioxolane a new chiral ligand for enantioselective catalysis
  作者：Giorgio Chelucci、M.Antonietta Cabras、Carlo Botteghi、Mauro Marchetti

  DOI：10.1016/s0957-4166(00)86190-x

  日期：1994.3

  The title compound (PYDIPHOS) has been prepared by a ten reaction sequence from dimethyl L-(+)-tartrate and checked in the palladium-catalyzed asymmetric hydroesterification of styrene and in the nickel catalyzed asymmetric cross-coupling reaction of 1-phenylethyl magnesium bromide with vinylbromide.