tert-butoxycarbonyloxyacetic acid methyl ester | 878395-91-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: tert-butoxycarbonyloxyacetic acid methyl ester
• 英文别名: methyl (tert-butoxycarbonyloxy)acetate；Boc-methyl glycolate；methyl O-Boc-hydroxyacetate；MeO2CCH2OBoc；2-((Tert-butoxycarbonyl)oxy)acetate；methyl 2-[(2-methylpropan-2-yl)oxycarbonyloxy]acetate
• CAS: 878395-91-6
• 化学式: C₈H₁₄O₅
• 分子量: 190.196
• InChiKey: LZLDHDVQEYUOLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butoxycarbonyloxyacetic acid methyl ester 在 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 4.0h， 生成 (Rs,2R,2'S)-methyl 2-(tert-butoxycarbonyloxy)-2-(3,3-dimethyl-1-tert-butanesulfinylaziridin-2-yl)acetate
  参考文献：
  名称：

  通过跨N-亚磺酰基-α-氯亚胺的顺-立体选择性曼尼希型加成 反应，不对称合成氯异苏氨酸衍生物†

  摘要：

  的曼尼希型反应ö跨手性-Boc乙醇酸酯类ñ -亚磺酰基- α-chloroaldimines导致高效且顺式新γ氯α羟基-β氨基酯（DR> 99：1）的合成-stereoselective。氯原子的α-配位能力对于曼尼希型反应的非对映选择性非常重要，并在过渡态模型中否决了亚硫酰氧与传入的E-烯酸酯的锂离子的螯合。这些新的氯异苏氨酸衍生物被证明是新型合成-β，γ-叠氮基-α-羟基酯和生物学相关的反式-恶唑烷酮羧酸酯的不对称合成的极好的构造单元。

  DOI：

  10.1039/c4ob00243a
• 作为产物：
  描述：

  羟乙酸甲酯 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 生成 tert-butoxycarbonyloxyacetic acid methyl ester
  参考文献：
  名称：

  通过跨N-亚磺酰基-α-氯亚胺的顺-立体选择性曼尼希型加成 反应，不对称合成氯异苏氨酸衍生物†

  摘要：

  的曼尼希型反应ö跨手性-Boc乙醇酸酯类ñ -亚磺酰基- α-chloroaldimines导致高效且顺式新γ氯α羟基-β氨基酯（DR> 99：1）的合成-stereoselective。氯原子的α-配位能力对于曼尼希型反应的非对映选择性非常重要，并在过渡态模型中否决了亚硫酰氧与传入的E-烯酸酯的锂离子的螯合。这些新的氯异苏氨酸衍生物被证明是新型合成-β，γ-叠氮基-α-羟基酯和生物学相关的反式-恶唑烷酮羧酸酯的不对称合成的极好的构造单元。

  DOI：

  10.1039/c4ob00243a

文献信息

• Total Synthesis of (−)-Haouamine B Pentaacetate and Structural Revision of Haouamine B
  作者：Yuichi Momoi、Kei-ichiro Okuyama、Hiroki Toya、Kenji Sugimoto、Kentaro Okano、Hidetoshi Tokuyama

  DOI：10.1002/anie.201407686

  日期：2014.11.24

  The enantiocontrolled total synthesis of (−)‐haouamine B pentaacetate was accomplished via an optically active indane‐fused β‐lactam, which was prepared by a newly developed Friedel–Crafts reaction. Subsequent cleavage of the β‐lactam and an intramolecular McMurry coupling reaction provided the core indane‐fused tetrahydropyridine, which led to the elucidation of the structure, as proposed by Trauner

  对映体控制的（-）-haouamine B五乙酸酯的全合成是通过光学活性的茚满-β-内酰胺完成的，这是由新开发的Friedel-Crafts反应制备的。随后β-内酰胺的裂解和分子内McMurry偶联反应提供了核心的茚满融合的四氢吡啶，从而阐明了结构，正如Trauner和Zubia所提出的那样。
• Synthetic Studies toward Haouamine B: Construction of Indenotetrahydropyridone Skeleton
  作者：Hidetoshi Tokuyama、Kei-ichiro Okuyama、Yuichi Momoi、Kenji Sugimoto、Kentaro Okano

  DOI：10.1055/s-0030-1259096

  日期：2011.1

  Synthetic studies on haouamine B are described. The characteristic indenotetrahydropyridone skeleton was constructed by intramolecular Friedel-Crafts alkylation of mesyloxy β-lactam derivative and intramolecular McMurry coupling as key processes.

  文中介绍了哈乌胺 B 的合成研究。通过介酰氧基δ-内酰胺衍生物的分子内 Friedel-Crafts 烷基化和分子内 McMurry 偶联作为关键过程，构建了特征性的茚四氢吡啶酮骨架。
• 10.1021/acs.oprd.4c00003
  作者：Peng, Feng、Qi, Ji、Zhang, Jin、Wang, Enkai、Cao, Xiaohui、Chen, Lu、Fan, Chao、Fan, Wei、Feng, Cheng、Lin, Mingxiang、Liu, Mingjie、Nawrat, Christopher C.、Schultz, Danielle M.、Song, Chaohui、Wang, Feng、Yin, Jingjun、Zhang, Yuming

  DOI：10.1021/acs.oprd.4c00003

  日期：——

  MK-7845 was designed as a 3C-like protease inhibitor for the treatment of COVID-19. To enable a rapid kilo-scale delivery of MK-7845 to accelerate its First-in-Human studies, we developed a fit-for-purpose process to produce two key building blocks in less than two months. The key discoveries were a highly diastereoselective Ellman addition route for β-aminoamide 6 and crystallization isolation methods

  MK-7845 被设计为一种类 3C 蛋白酶抑制剂，用于治疗 COVID-19。为了能够快速交付公斤级的 MK-7845，以加速其首次人体研究，我们开发了一种适合用途的工艺，可在不到两个月的时间内生产出两个关键的构建模块。关键发现是β-氨基酰胺6的高度非对映选择性埃尔曼加成路线以及在良好质量控制下生产6和酸9的结晶分离方法。
• Rapid Assembly of the Polyhydroxylated β-Amino Acid Constituents of Microsclerodermins C, D, and E
  作者：Thomas Hjelmgaard、Sophie Faure、Pascale Lemoine、Bernard Viossat、David J. Aitken

  DOI：10.1021/ol702962z

  日期：2008.3.1

  A very short and efficient synthesis of protected derivatives of APTO and AETD, the complex polyhydroxylated beta-amino acid residues present in microsclerodermins C, D, and E, is described. The targets are obtained in only five steps, in 23% and 16% overall yields, respectively. The key transformation involves the completely diastereoselective two-carbon homologation of appropriately selected intermediate chiral sulfinimines.
• Highly Diastereoselective Enolate Addition of O-Protected α-Hydroxyacetate to (<i>S</i><i>_R</i>)-<i>tert-</i>Butanesulfinylimines:  Synthesis of Taxol Side Chain
  作者：Yin Wang、Qin-Fei He、Hao-Wei Wang、Xuan Zhou、Zhi-Yan Huang、Yong Qin

  DOI：10.1021/jo052298n

  日期：2006.2.1

  [GRAPHICS]The taxol side chain (S-R,2R,3S)-N-tert-butanesulfinyl-O-Boe-3-phenylisoserine benzyl ester 4c was synthesized through a lithium enolate addition of O-Boc-alpha-hydroxyacetate benzyl ester 5c to benzylidene (S-R)-tert-butanesulfinamide 6a in excellent yield and diastereoselectivity. By similar approach, a series of enantiopure 3-substituted isoserine benzyl esters 4 useful for the semi-syntheses of taxol derivatives were also prepared in high to excellent yields and diastereoselectivities. The diastereoselective addition mechanism was discussed on the basis of the experimental observation.