(3S,4R)-1-[bis(trimethylsilyl)methyl]-4-phenyl-3-[(4S,5R)-4,5-diphenyl-2-oxo-oxazolidin-3-yl]-azetidin-2-one | 198022-17-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (3S,4R)-1-[bis(trimethylsilyl)methyl]-4-phenyl-3-[(4S,5R)-4,5-diphenyl-2-oxo-oxazolidin-3-yl]-azetidin-2-one
• 英文别名: (4S,5R)-3-[(3S,4R)-1-[bis(trimethylsilyl)methyl]-2-oxo-4-phenylazetidin-3-yl]-4,5-diphenyl-1,3-oxazolidin-2-one
• CAS: 198022-17-2
• 化学式: C₃₁H₃₈N₂O₃Si₂
• 分子量: 542.825
• InChiKey: CRJOCWAGVDIKOD-WXIAYYLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.0
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4R)-1-[bis(trimethylsilyl)methyl]-4-phenyl-3-[(4S,5R)-4,5-diphenyl-2-oxo-oxazolidin-3-yl]-azetidin-2-one 、 碘甲烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 16.17h， 以84%的产率得到(4R)-3-methyl-1-[bis(trimethylsilyl)methyl]-4-phenyl-3-[(4S,5R)-4,5-diphenyl-2-oxo-oxazolidin-3-yl]-azetidin-2-one
  参考文献：
  名称：

  Synthesis of Type II β-Turn Surrogate Dipeptides Based on syn-α-Amino-α,β-dialkyl-β-lactams

  摘要：

  The achiral bis(trimethylsilyl)methyl group acts as an efficient stereochemical determinant of the alpha-alkylation reaction in beta-branched alpha-phenyloxazolidinyl- or alpha-diphenyloxazolidinyl-beta-lactams and provides the first stereocontrolled access to syn-alpha-amino-alpha,beta-dialkyl(aryl)-beta-lactams. These products are readily transformed into type II beta-turn mimetic surrogates 2B.

  DOI：

  10.1021/ol048348c
• 作为产物：
  描述：

  二(三甲基硅基)甲胺 在 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 20.5h， 生成 (3S,4R)-1-[bis(trimethylsilyl)methyl]-4-phenyl-3-[(4S,5R)-4,5-diphenyl-2-oxo-oxazolidin-3-yl]-azetidin-2-one
  参考文献：
  名称：

  A Contribution to the Asymmetric Synthesis of 3-Amino β-Lactams: The Diastereoselective [2+2] Cycloaddition Reaction of Chiral Aminoketene Equivalents with Enolizable Aldehyde-Derived Imines

  摘要：

  AbstractN‐[Bis(trimethylsilyl)methyl]imines 9 show unique chemical properties when compared with conventional imines. Their reaction with optically pure aminoketenes derived from dehydrochlorination of 14 and 15 affords the corresponding 3‐amino‐4‐alkyl‐β‐lactams 16 and 17 in good yields and high diastereoselectivities. The mild deprotection of bis(trimethylsilyl)methyl‐ and phenyloxazolidinone moieties with, respectively, cerium(IV) ammonium nitrate and lithium/ammonia or hydrogen/Pd(OH)2 allows the preparation of a variety of β‐lactam antibiotic building blocks.

  DOI：

  10.1002/chem.19970030909

文献信息

• A Contribution to the Asymmetric Synthesis of 3-Amino β-Lactams: The Diastereoselective [2+2] Cycloaddition Reaction of Chiral Aminoketene Equivalents with Enolizable Aldehyde-Derived Imines
  作者：Claudio Palomo、Jesus M. Aizpurua、Marta Legido、Antonia Mielgo、Regina Galarza

  DOI：10.1002/chem.19970030909

  日期：1997.9

  AbstractN‐[Bis(trimethylsilyl)methyl]imines 9 show unique chemical properties when compared with conventional imines. Their reaction with optically pure aminoketenes derived from dehydrochlorination of 14 and 15 affords the corresponding 3‐amino‐4‐alkyl‐β‐lactams 16 and 17 in good yields and high diastereoselectivities. The mild deprotection of bis(trimethylsilyl)methyl‐ and phenyloxazolidinone moieties with, respectively, cerium(IV) ammonium nitrate and lithium/ammonia or hydrogen/Pd(OH)2 allows the preparation of a variety of β‐lactam antibiotic building blocks.
• Synthesis of Type II β-Turn Surrogate Dipeptides Based on <i>s</i><i>yn</i>-α-Amino-α,β-dialkyl-β-lactams
  作者：Claudio Palomo、Jesus M. Aizpurua、Iñaki Ganboa、Ana Benito、Lourdes Cuerdo、Raluca M. Fratila、Azucena Jimenez、Iraida Loinaz、José I. Miranda、Kinga R. Pytlewska、Andreea Micle、Anthony Linden

  DOI：10.1021/ol048348c

  日期：2004.11.1

  The achiral bis(trimethylsilyl)methyl group acts as an efficient stereochemical determinant of the alpha-alkylation reaction in beta-branched alpha-phenyloxazolidinyl- or alpha-diphenyloxazolidinyl-beta-lactams and provides the first stereocontrolled access to syn-alpha-amino-alpha,beta-dialkyl(aryl)-beta-lactams. These products are readily transformed into type II beta-turn mimetic surrogates 2B.