tert-butyl N-[(1S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylmethoxyethyl]carbamate | 412915-38-9

• 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: tert-butyl N-[(1S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylmethoxyethyl]carbamate
• CAS: 412915-38-9
• 化学式: C₁₉H₂₉NO₅
• 分子量: 351.443
• InChiKey: DBHFMCOLOTUTSI-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 tert-butyl N-[(1S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylmethoxyethyl]carbamate 在 sodium 、 ruthenium(IV) oxide 、 sodium periodate 作用下， 以 氨 、 四氯化碳 、 水 、 乙腈 、 乙醚 为溶剂， 以72%的产率得到methyl (2R)-2-[(tert-butylcarbonyl)amino]-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanoate
  参考文献：
  名称：

  Efficient synthesis of (2R,3S)- and (2S,3S)-2-amino-1,3,4-butanetriols through stereodivergent hydroxymethylation of d-glyceraldehyde nitrones

  摘要：

  The nucleophilic addition of two alkoxymethyllithium derivatives to three D-glyceraldchyde derived nitrones has been investigated. The diastereofacial selectivity of the reaction could be controlled by the appropriate use of Lewis acids as precomplexing agents of the nitrones. The obtained syn and anti adducts were further converted into C-4 building blocks and beta-hydroxy-alpha-aminoacids. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02191-8
• 作为产物：
  描述：

  N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone 在 palladium hydroxide - carbon 氢气 、 氯化二乙基铝 作用下， 以 四氢呋喃 、 甲醇 为溶剂， -80.0~20.0 ℃ 、10.34 MPa 条件下， 反应 24.25h， 生成 tert-butyl N-[(1S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylmethoxyethyl]carbamate
  参考文献：
  名称：

  Efficient synthesis of (2R,3S)- and (2S,3S)-2-amino-1,3,4-butanetriols through stereodivergent hydroxymethylation of d-glyceraldehyde nitrones

  摘要：

  The nucleophilic addition of two alkoxymethyllithium derivatives to three D-glyceraldchyde derived nitrones has been investigated. The diastereofacial selectivity of the reaction could be controlled by the appropriate use of Lewis acids as precomplexing agents of the nitrones. The obtained syn and anti adducts were further converted into C-4 building blocks and beta-hydroxy-alpha-aminoacids. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02191-8

文献信息

• Efficient synthesis of (2R,3S)- and (2S,3S)-2-amino-1,3,4-butanetriols through stereodivergent hydroxymethylation of d-glyceraldehyde nitrones
  作者：Pedro Merino、Santiago Franco、Francisco L. Merchan、Julia Revuelta、Tomas Tejero

  DOI：10.1016/s0040-4039(01)02191-8

  日期：2002.1

  The nucleophilic addition of two alkoxymethyllithium derivatives to three D-glyceraldchyde derived nitrones has been investigated. The diastereofacial selectivity of the reaction could be controlled by the appropriate use of Lewis acids as precomplexing agents of the nitrones. The obtained syn and anti adducts were further converted into C-4 building blocks and beta-hydroxy-alpha-aminoacids. (C) 2002 Elsevier Science Ltd. All rights reserved.