(2S,3R)-tert-butyl 3-hydroxy-2-isobutyl-5-oxopyrrolidine-1-carboxylate | 936226-65-2

• 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: (2S,3R)-tert-butyl 3-hydroxy-2-isobutyl-5-oxopyrrolidine-1-carboxylate
• 英文别名: tert-butyl (2S,3R)-3-hydroxy-2-(2-methylpropyl)-5-oxopyrrolidine-1-carboxylate
• CAS: 936226-65-2
• 化学式: C₁₃H₂₃NO₄
• 分子量: 257.33
• InChiKey: HYAQUMODGYTCDT-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R)-tert-butyl 3-hydroxy-2-isobutyl-5-oxopyrrolidine-1-carboxylate 在 sodium hydroxide 、 水 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以75%的产率得到(3R,4S)-4-[[(1,1-二甲基乙氧基)羰基]氨基]-3-羟基-6-甲基-庚酸
  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：

  (2S,3R)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-isobutyl-5-oxopyrrolidine-1-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以43%的产率得到(2S,3R)-tert-butyl 3-hydroxy-2-isobutyl-5-oxopyrrolidine-1-carboxylate
  参考文献：
  名称：

  通过立体选择性串联Barbier过程反式-4-羟基-5-取代的2-吡咯烷酮 的有效方法：（3 R，4 S）-他汀类药物，（+）-普鲁酶和（-）-hapalosin †的不同合成

  摘要：

  通过立体选择性串联Barbier过程（R，S RS）-8与烷基和芳基的对映体，开发了一种非对映选择性的方法，用于反式-4-羟基-5-取代的2-吡咯烷酮1（P 1 = TBS，P 2 = H）溴化物。反式-4-羟基-5-取代的2-吡咯烷酮在C-5立体中心的立体化学仅受α-烷氧基取代的控制。这种有效的方法已成功用于制备各种取代的（3 R，4 S）-statines 2。此外，两种具有（+）-preussin 4的生物活性天然产物通过这种立体选择性串联Barbier方法有效地合成了Hapalosin 5和Hapalosin 5。

  DOI：

  10.1039/c6ob02523d

文献信息

• Cu‐Catalyzed Asymmetric Kinetic Boron Conjugate Addition of γ‐Substituted α,β‐Unsaturated γ‐Lactams
  作者：Liang Tang、Yicong Luo、Cheng Sheng、Fang Xie、Wanbin Zhang

  DOI：10.1002/anie.202304640

  日期：2023.6.19

  A Cu-catalyzed asymmetric kinetic boron conjugate addition of γ-substituted α,β-unsaturated γ-lactams followed by oxidation is reported with good results. This strategy provides an efficient access to valuable enantioenriched α,β-unsaturated γ-lactams bearing simple γ-alkyl or aryl substituents, which showed inhibitory activities against cisplatin-sensitive ovarian cancer cells A2780. A new Lewis acid

  据报道，Cu 催化的 γ-取代的 α,β-不饱和 γ-内酰胺的不对称动态硼共轭加成反应随后进行氧化，取得了良好的结果。该策略提供了一种有效获得有价值的对映体富集的α,β-不饱和γ-内酰胺的途径，该内酰胺带有简单的γ-烷基或芳基取代基，其对顺铂敏感的卵巢癌细胞A2780表现出抑制活性。提出了一种新的路易斯酸铜催化机理。
• Symplocin A, a Linear Peptide from the Bahamian Cyanobacterium<i>Symploca</i>sp. Configurational Analysis of<i>N</i>,<i>N</i>-Dimethylamino Acids by Chiral-Phase HPLC of Naphthacyl Esters
  作者：Tadeusz F. Molinski、Kirk A. Reynolds、Brandon I. Morinaka

  DOI：10.1021/np200861n

  日期：2012.3.23

  The absolute stereostructures of the components of symplocin A (3), a new N,N-dimethyl-terminated peptide from the Bahamian cyanobacterium Symploca sp., were assigned from spectroscopic analysis, including MS, 2D NMR, and Marfey's analysis. The complete absolute configuration of symplocin A, including the unexpected D-configurations of the terminal N,N-dimethylisoleucine and valic acid residues, was assigned by chiral-phase HPLC of the corresponding 2-naphthacyl esters, a highly sensitive, complementary strategy for assignment of N-blocked peptide residues where Marfey's method is ineffectual or other methods fall short. Symplocin A exhibited potent activity as an inhibitor of cathepsin E (IC50 300 pM).
• An efficient approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones through a stereoselective tandem Barbier process: divergent syntheses of (3R,4S)-statines, (+)-preussin and (−)-hapalosin
  作者：Chang-Mei Si、Lu-Ping Shao、Zhuo-Ya Mao、Wen Zhou、Bang-Guo Wei

  DOI：10.1039/c6ob02523d

  日期：——

  diastereoselective approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones 1 (P1 = TBS, P2 = H) has been developed through a stereoselective tandem Barbier process of (R,SRS)-8 with alkyl and aryl bromide. The stereochemistry at the C-5 stereogenic center of the trans-4-hydroxy-5-substituted 2-pyrrolidinones was solely controlled by α-alkoxy substitution. This effective approach was successfully used

  通过立体选择性串联Barbier过程（R，S RS）-8与烷基和芳基的对映体，开发了一种非对映选择性的方法，用于反式-4-羟基-5-取代的2-吡咯烷酮1（P 1 = TBS，P 2 = H）溴化物。反式-4-羟基-5-取代的2-吡咯烷酮在C-5立体中心的立体化学仅受α-烷氧基取代的控制。这种有效的方法已成功用于制备各种取代的（3 R，4 S）-statines 2。此外，两种具有（+）-preussin 4的生物活性天然产物通过这种立体选择性串联Barbier方法有效地合成了Hapalosin 5和Hapalosin 5。
• 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.