(2-benzylallyl)trichlorostannane | 251362-56-8

• 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: (2-benzylallyl)trichlorostannane
• 英文别名: Stannane, trichloro[2-(phenylmethyl)-2-propenyl]-；2-benzylprop-2-enyl(trichloro)stannane
• CAS: 251362-56-8
• 化学式: C₁₀H₁₁Cl₃Sn
• 分子量: 356.266
• InChiKey: CQNISNVDWIKTCB-UHFFFAOYSA-K

物化性质

• 沸点：
  357.3±31.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (2-benzylallyl)trichlorostannane 在 咪唑 、 lithium hydroxide 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 dimethyl sulfide borane 、 四丁基氟化铵 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-{(2R,4S,5S)-2-苯甲基-5-[(叔-丁氧基羰基)氨基]-4-羟基-6-苯基己酰}-L-亮氨酰-L-苯丙氨酸酰胺
  参考文献：
  名称：

  Short Total Synthesis of Aspartyl Protease Inhibitors L-685,434, L-682,679 and L-685,458

  摘要：

  羟乙基二肽等效体L-685,434、L-682,679和L-685,458通过一系列步骤合成，包括与烯丙基三氯锡烷的偶联反应生成α-氨基醛，随后对相应的1,2-顺式和1,2-反式氨基醇进行硼氢化反应生成二醇，在TPAP条件下内酯化，内酯开环并与所需胺或二肽酰胺进行肽偶联反应。

  DOI：

  10.1055/s-2002-34891

文献信息

• An efficient procedure for the synthesis of 2-N-Boc-amino-3,5-diols
  作者：Luiz C. Dias、Juliana Fattori、Carla C. Perez、Vanda M. de Oliveira、Andrea M. Aguilar

  DOI：10.1016/j.tet.2008.04.049

  日期：2008.6

  AWe wish to describe here the diastereoselective reaction between chiral N-Boc-alpha-amino aldehydes with both achiral allyltrichlorostannanes leading to 1,2-syn-N-Boc-alpha-amino alcohols, which are easily converted to the corresponding 4-N-Boc-amino-3-hydroxy ketones after treatment with catalytic amounts of OsO4 in the presence of NaIO4. After reduction of the carbonyl function, these 4-N-Boc-amino-3-hydroxy ketones were converted to 1-deoxy-5-hydroxy sphingosine analogues. (C) 2008 Elsevier Ltd. All rights reserved.
• Addition of allyltrichlorostannanes to aldehydes: application in the synthesis of 4-N-Boc-amino-3-hydroxy ketones
  作者：Luiz C. Dias、Juliana Fattori、Carla Cristina Perez

  DOI：10.1016/j.tetlet.2007.11.072

  日期：2008.1

  We wish to describe here the diastereoselective reaction between chiral N-Boc-alpha-amino aldehydes and achiral allyltrichlorostannanes leading to 1,2-syn-N-Boc-alpha-amino alcohols, which are treated with catalytic amounts of OSO4 in the presence of NaIO4 to provide the corresponding 4-N-Boc-amino-3-hydroxy ketones. (C) 2007 Elsevier Ltd. All rights reserved.
• Allyltrichlorostannane additions to chiral aldehydes
  作者：Luiz Carlos Dias、Débora Ribeiro dos Santos、Leonardo José Steil

  DOI：10.1016/s0040-4039(03)01713-1

  日期：2003.9

  Chiral and achiral allyltrichlorostannanes reacted with chiral beta-alkoxy and syn and anti alpha-methyl-beta-alkoxy aldehydes to give the corresponding homoallylic alcohols with moderate to high diastereoselectivities. (C) 2003 Elsevier Ltd. All rights reserved.
• Addition of lactate-derived chiral allyltrichlorostannanes to chiral aldehydes
  作者：Luiz C. Dias、Leonardo J. Steil

  DOI：10.1016/j.tetlet.2004.09.186

  日期：2004.11

  Chiral lactate-derived allyltrichlorostannanes reacted with chiral alpha-methyl beta-alkoxy and syn and anti alpha-methyl-beta-alkoxy aldehydes to give the corresponding homoallylic alcohols with moderate to high 1,4-syn-diastereoselectivities. (C) 2004 Elsevier Ltd. All rights reserved.
• Short Total Synthesis of Aspartyl Protease Inhibitors L-685,434, L-682,679 and L-685,458
  作者：Luiz C. Dias、Andrea A. Ferreira、Gaspar Diaz

  DOI：10.1055/s-2002-34891

  日期：——

  Hydroxyethylene dipeptide isosteres L-685,434, L-682,679 and L-685,458 were synthesized in a few steps by a sequence involving an allyltrichlorostannane coupling with an α-aminoaldehyde followed by hydroboration of the corresponding 1,2-syn and 1,2-anti aminoalcohols to give the diols, lactonization under TPAP conditions, lactone opening and peptide coupling with the desired amine or dipeptide amide.

  羟乙基二肽等效体L-685,434、L-682,679和L-685,458通过一系列步骤合成，包括与烯丙基三氯锡烷的偶联反应生成α-氨基醛，随后对相应的1,2-顺式和1,2-反式氨基醇进行硼氢化反应生成二醇，在TPAP条件下内酯化，内酯开环并与所需胺或二肽酰胺进行肽偶联反应。