(4R)-4-benzyl-3-[(2R,3S,4S)-5-[tert-butyl(diphenyl)silyl]oxy-3-hydroxy-4-methyl-2-phenylmethoxypentanoyl]-1,3-oxazolidin-2-one | 1190618-84-8

• 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: (4R)-4-benzyl-3-[(2R,3S,4S)-5-[tert-butyl(diphenyl)silyl]oxy-3-hydroxy-4-methyl-2-phenylmethoxypentanoyl]-1,3-oxazolidin-2-one
• CAS: 1190618-84-8
• 化学式: C₃₉H₄₅NO₆Si
• 分子量: 651.875
• InChiKey: STPVMUFQZDSJSQ-VZLVNQQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  47
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R)-4-benzyl-3-[(2R,3S,4S)-5-[tert-butyl(diphenyl)silyl]oxy-3-hydroxy-4-methyl-2-phenylmethoxypentanoyl]-1,3-oxazolidin-2-one 、 二甲羟胺盐酸盐 在 三甲基铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.25h， 以81%的产率得到
  参考文献：
  名称：

  Asymmetric synthesis of the core of AMPTD, the key amino acid of microsclerodermins F-I

  摘要：

  We report a stereoselective synthesis of the five consecutive stereocenters of AMPTD in seven steps. Highlights include an Evans glycolate aldol reaction, the use of a Weinreb amide as an aldehyde masking group, and a Mannich reaction with an Ellman-type chiral sulfimine. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.144
• 作为产物：
  描述：

  (2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal 、 (4R)-3-[2-(Phenylmethoxy)acetyl]-4-(phenylmethyl)oxazolidin-2-one 在 三氟甲磺酸二丁硼 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到(4R)-4-benzyl-3-[(2R,3S,4S)-5-[tert-butyl(diphenyl)silyl]oxy-3-hydroxy-4-methyl-2-phenylmethoxypentanoyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Asymmetric synthesis of the core of AMPTD, the key amino acid of microsclerodermins F-I

  摘要：

  We report a stereoselective synthesis of the five consecutive stereocenters of AMPTD in seven steps. Highlights include an Evans glycolate aldol reaction, the use of a Weinreb amide as an aldehyde masking group, and a Mannich reaction with an Ellman-type chiral sulfimine. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.144

文献信息

• Asymmetric synthesis of the core of AMPTD, the key amino acid of microsclerodermins F-I
  作者：Cameron M. Burnett、Robert M. Williams

  DOI：10.1016/j.tetlet.2009.06.144

  日期：2009.9

  We report a stereoselective synthesis of the five consecutive stereocenters of AMPTD in seven steps. Highlights include an Evans glycolate aldol reaction, the use of a Weinreb amide as an aldehyde masking group, and a Mannich reaction with an Ellman-type chiral sulfimine. (C) 2009 Elsevier Ltd. All rights reserved.