(+)-N-(triisopropylsilyl)-L-methioninaldehyde | 1006035-72-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (+)-N-(triisopropylsilyl)-L-methioninaldehyde
• 英文别名: N-TIPS-(L)-methioninal；(2S)-4-methylsulfanyl-2-[tri(propan-2-yl)silylamino]butanal
• CAS: 1006035-72-8
• 化学式: C₁₄H₃₁NOSSi
• 分子量: 289.558
• InChiKey: ZGHYSSJEQGBKBJ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  B-allyl-(10S)-trimethylsilyl-9-borabicyclo[3.3.2]decane 、 (+)-N-(triisopropylsilyl)-L-methioninaldehyde 在 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.5h， 生成 C₁₇H₃₇NOSSi
  参考文献：
  名称：

  Strict Reagent Control in the Asymmetric Allylboration of N-TIPS-α-Amino Aldehydes with the B-Allyl-10-TMS-9-borabicyclo[3.3.2]decanes

  摘要：

  The allylboration of enantiomerically pure N-triisopropylsilyl-alpha-amino aldehydes (2) with B-allyl-10-trimethylsilyl-9-borabicyclo[3.3.2]decanes (1) proceeds cleanly at -78 degrees C, exhibiting essentially complete reagent control. After an oxidative workup, an HOAc-mediated N-->O TIPS rearrangement facilitates the clean formation of stable O-TIPS protected beta-amino alcohol derivatives 3 which are isolated in 60-83% yields in >= 96% de and >99% ee. For the leucinal series (R = i-Bu), an efficient entry to either statine (8aSS) or epi-statine (8aRS) is reported illustrating the versatility of this potent 1/2 combination.

  DOI：

  10.1021/ol802685e
• 作为产物：
  描述：

  以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 5.0h， 以1.77 g的产率得到(+)-N-(triisopropylsilyl)-L-methioninaldehyde
  参考文献：
  名称：

  Enantiomerically Pure α-Amino Aldehydes from Silylated α-Amino Acids

  摘要：

  The disilylation of alpha-amino acids 1 to provide 2 (72-87%) was achieved without racemization. An unprecedented borane-mediated semi-reduction strategy was devised to convert 2 to stable, isolable oxazaborolidines 3 (100%) which were hydrolyzed to provide 5 (49-60%) as pure, stable compounds. Analysis of the Mosher amides (8) of the gamma-amino esters 7 reveals that <= 2% racemization occurs in the 1 -> 8 conversions.

  DOI：

  10.1021/ol7028993

文献信息

• Enantiomerically Pure α-Amino Aldehydes from Silylated α-Amino Acids
  作者：Buddy Soto-Cairoli、Jorge Justo de Pomar、John A. Soderquist

  DOI：10.1021/ol7028993

  日期：2008.1.1

  The disilylation of alpha-amino acids 1 to provide 2 (72-87%) was achieved without racemization. An unprecedented borane-mediated semi-reduction strategy was devised to convert 2 to stable, isolable oxazaborolidines 3 (100%) which were hydrolyzed to provide 5 (49-60%) as pure, stable compounds. Analysis of the Mosher amides (8) of the gamma-amino esters 7 reveals that <= 2% racemization occurs in the 1 -> 8 conversions.
• Strict Reagent Control in the Asymmetric Allylboration of <i>N</i>-TIPS-α-Amino Aldehydes with the <i>B-</i>Allyl-10-TMS-9-borabicyclo[3.3.2]decanes
  作者：Buddy Soto-Cairoli、John A. Soderquist

  DOI：10.1021/ol802685e

  日期：2009.1.15

  The allylboration of enantiomerically pure N-triisopropylsilyl-alpha-amino aldehydes (2) with B-allyl-10-trimethylsilyl-9-borabicyclo[3.3.2]decanes (1) proceeds cleanly at -78 degrees C, exhibiting essentially complete reagent control. After an oxidative workup, an HOAc-mediated N-->O TIPS rearrangement facilitates the clean formation of stable O-TIPS protected beta-amino alcohol derivatives 3 which are isolated in 60-83% yields in >= 96% de and >99% ee. For the leucinal series (R = i-Bu), an efficient entry to either statine (8aSS) or epi-statine (8aRS) is reported illustrating the versatility of this potent 1/2 combination.