(4S,5S)-(+)-N-tert-butyloxycarbonyl-4-hydroxymethyl-5-(triisopropylsilyloxymethyl) pyrrolidin-2-one | 222307-21-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (4S,5S)-(+)-N-tert-butyloxycarbonyl-4-hydroxymethyl-5-(triisopropylsilyloxymethyl) pyrrolidin-2-one
• 英文别名: tert-butyl (2S,3S)-3-(hydroxymethyl)-5-oxo-2-[tri(propan-2-yl)silyloxymethyl]pyrrolidine-1-carboxylate
• CAS: 222307-21-3
• 化学式: C₂₀H₃₉NO₅Si
• 分子量: 401.619
• InChiKey: HTGNVJHEYGZPSE-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5S)-(+)-N-tert-butyloxycarbonyl-4-hydroxymethyl-5-(triisopropylsilyloxymethyl) pyrrolidin-2-one 在 盐酸 、 二乙胺基三氟化硫 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 (4S,5S)-(+)-N-tert-butyloxycarbonyl-4-fluoromethyl-5-(hydroxymethyl) pyrrolidin-2-one
  参考文献：
  名称：

  Photoinduced addition of methanol to 5(S)-5-triisopropylsiloxymethyl-N-boc-dihydropyrrole-2(5H)-one: A new route to 4(S), 5(S)-disubstituted pyrrolidin-2-ones

  摘要：

  We describe the photoinduced addition of methanol to 5(S)-5-triisopropylsiloxymethyl-N-boc-dihydropyrrole-2(5H)-one to produce 5(S)-triisopropylsiloxymethyl-4( S)-hydroxymethylpyrrolidine-2-one, and conversion of this into a variety of 4( S), S(S)-pyrrolidine-2-ones. Photoinduced addition of methanol to 5(R)-N-boc-5-amino-dihydropyran-2(5H)-one yielded the unexpected product 4(S)-1'-[2'-hydroxy, 1'-( R)-N-boc-amino]ethyl-tetrahydrofuran-2-one via rearrangement of the initial photoadduct. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01094-1
• 作为产物：
  描述：

  (S)-(+)-N-tert-butyloxycarbonyl-5-(triisopropylsilyloxymethyl)-pyrrolidin-2-one 在 二苯甲酮 、 间氯过氧苯甲酸 、 lithium hexamethyldisilazane 作用下， 以 二氯甲烷 为溶剂， 反应 32.0h， 生成 (4S,5S)-(+)-N-tert-butyloxycarbonyl-4-hydroxymethyl-5-(triisopropylsilyloxymethyl) pyrrolidin-2-one
  参考文献：
  名称：

  Photoinduced addition of methanol to 5(S)-5-triisopropylsiloxymethyl-N-boc-dihydropyrrole-2(5H)-one: A new route to 4(S), 5(S)-disubstituted pyrrolidin-2-ones

  摘要：

  We describe the photoinduced addition of methanol to 5(S)-5-triisopropylsiloxymethyl-N-boc-dihydropyrrole-2(5H)-one to produce 5(S)-triisopropylsiloxymethyl-4( S)-hydroxymethylpyrrolidine-2-one, and conversion of this into a variety of 4( S), S(S)-pyrrolidine-2-ones. Photoinduced addition of methanol to 5(R)-N-boc-5-amino-dihydropyran-2(5H)-one yielded the unexpected product 4(S)-1'-[2'-hydroxy, 1'-( R)-N-boc-amino]ethyl-tetrahydrofuran-2-one via rearrangement of the initial photoadduct. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01094-1

文献信息

• Photoinduced addition of methanol to 5(S)-5-triisopropylsiloxymethyl-N-boc-dihydropyrrole-2(5H)-one: A new route to 4(S), 5(S)-disubstituted pyrrolidin-2-ones
  作者：Michael G.B. Drew、R.John Harrison、John Mann、Allen J. Tench、Robert J. Young

  DOI：10.1016/s0040-4020(98)01094-1

  日期：1999.1

  We describe the photoinduced addition of methanol to 5(S)-5-triisopropylsiloxymethyl-N-boc-dihydropyrrole-2(5H)-one to produce 5(S)-triisopropylsiloxymethyl-4( S)-hydroxymethylpyrrolidine-2-one, and conversion of this into a variety of 4( S), S(S)-pyrrolidine-2-ones. Photoinduced addition of methanol to 5(R)-N-boc-5-amino-dihydropyran-2(5H)-one yielded the unexpected product 4(S)-1'-[2'-hydroxy, 1'-( R)-N-boc-amino]ethyl-tetrahydrofuran-2-one via rearrangement of the initial photoadduct. (C) 1999 Elsevier Science Ltd. All rights reserved.