Boc-L-alanine-2-bromoethyl ester | 65538-68-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Boc-L-alanine-2-bromoethyl ester
• 英文别名: tert-butoxycarbonyl-L-alanine 2-bromoethyl ester；2-bromoethyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 65538-68-3
• 化学式: C₁₀H₁₈BrNO₄
• 分子量: 296.161
• InChiKey: YYHWLUPDLAQGJP-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Boc-L-alanine-2-bromoethyl ester 在 4-二甲氨基吡啶 、 potassium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成
  参考文献：
  名称：

  Design, synthesis and evaluation of novel scutellarin and scutellarein-N,N-bis-substituted carbamate-l-amino acid derivatives as potential multifunctional therapeutics for Alzheimer’s disease

  摘要：

  DOI：

  10.1016/j.bioorg.2022.105760
• 作为产物：
  描述：

  氟甲酸叔丁酯 在 三乙胺 作用下， 以 正戊烷 为溶剂， 生成 Boc-L-alanine-2-bromoethyl ester
  参考文献：
  名称：

  Protection of functional groups during reaction and their subsequent

  摘要：

  在制备具有公式A' -- X的有机化合物的过程中，其中X是氨基、羟基或羧基，而A'是分子的剩余部分，从具有公式A -- X的有机化合物开始，其中A是可以发生反应形成A'的分子的剩余部分，通过将A -- X转化为具有公式A -- Z -- COOR的化合物，其中Z是--NH--、--O--或直接的C--C键，R是具有##STR1##的基团，其中Y是直接的C--C单键，--CH.dbd.CH--基团或芳基基团，R.sup.1到R.sup.4各自独立地是氢、卤素或烷基、芳基、芳基烷基、烷氧羰基、烷基氨基羰基、芳基氨基羰基或环烷基氨基羰基基团，或R.sup.1 + r.sup.2和R.sup.3 + R.sup.4各自独立地完成一个5-或6-成员的碳环，或R.sup.1和R.sup.3与基团--C--Y--C--共同形成具有5或6个碳原子的碳环，Hal是卤素，从而保护X，然后将A -- Z -- COOR转化为具有公式A' -- Z -- COOR的化合物，然后处理化合物A' -- Z -- COOR以恢复基团X，改进包括使用一价钴络合物的碱金属化合物对化合物A' -- Z -- COOR进行处理。该过程特别适用于氨基羧酸，包括青霉素和头孢菌素合成各阶段的中间体。

  公开号：

  US04111933A1

文献信息

• Design and synthesis of novel bis(l-amino acid) ester prodrugs of 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA) with improved anti-HBV activity
  作者：Xiaozhong Fu、Saihong Jiang、Chuan Li、Jian Xin、Yushe Yang、Ruyun Ji

  DOI：10.1016/j.bmcl.2006.10.021

  日期：2007.1

  A series of novel bis(L-amino acid) ester prodrugs of 9-[2-(phosphonomethoxy)ethyl] adenine (PMEA) was synthesized and their anti-HBV activity was evaluated in HepG 2 2.2.15 cells. Compounds 11, 12, 21, 22, 26, and 27 demonstrated more potent anti-HBV activity and higher selective index (SI) than adefovir dipivoxil, which was used as a positive control. Compound 11, which was found to be the most potent

  合成了一系列新型的9- [2-（膦酰基甲氧基）乙基]腺嘌呤（PMEA）双（L-氨基酸）酯前药，并在HepG 2 2.2.15细胞中评估了它们的抗HBV活性。与用作阳性对照的阿德福韦酯相比，化合物11、12、21、22、26和27表现出更强的抗HBV活性和更高的选择性指数（SI）。被发现是最有效的化合物11，其效力是阿德福韦酯的5倍，EC50值为0.095 microM，CC50值为6636 microM。化合物11的SI值（> 69,000）分别比阿德福韦酯和拉米夫定高60倍和24倍。体外稳定性研究表明，化合物11比阿德福韦酯更稳定，t1 / 2为270分钟。
• Chemoenzymatic Synthesis of Nucleopeptides
  作者：Stefanie Flohr、Volker Jungmann、Herbert Waldmann

  DOI：10.1002/(sici)1521-3765(19990201)5:2<669::aid-chem669>3.0.co;2-v

  日期：1999.2.1

  Nucleoproteins, in which the hydroxy group of a serine, a threonine, or a tyrosine, is linked through a phosphodiester group to the 3'- or 5'-end of DNA or RNA, play decisive roles in important biological processes. They may even have a major part in the process of viral replication by nucleoprotein-primed elongation of the oligonucleotide strand. For the study of the biological phenomena, in which nucleoproteins are involved, nucleopeptides with the characteristic linkage between the peptide chain and the oligonucleotide of their parent nucleoproteins may serve as powerful tools. However, the synthesis of these compounds is complicated by their pronounced acid- and base-lability, as well as their multifunctionality. As a result, protecting groups, which can be removed under the mildest conditions, are required. For the construction of such peptide conjugates using a flexible building block strategy, a combination of enzyme-labile and chemical protecting groups was developed. The C-terminal blocking function can be removed selectively from fully protected nucleoamino acid methyl, 2-methoxyethyl (ME), and methoxyethoxyethyl (MEE) esters by saponification of the esters. After elongation of the peptide chain with amino acid or peptide methyl, ME, MEE, and choline esters, the C-terminal ester blocking group can again be removed easily. The methyl, ME, and MEE esters are cleaved off with lipase, and the choline ester group is selectively attacked by butyrylcholine esterase. The nucleoamino acids and peptides formed may be fully deprotected. To this end, the enzyme-labile N-phenylacetyl (PhAc) group, which was employed to mask the amino functions of the nucleobases, was removed. The O-acetate in the deoxyribose was saponified, and the allyl protecting groups present were cleaved by Pd-0-mediated allyl transfer. By combination of these techniques, a nucleopeptide was produced, which represents the characteristic linkage region of the nucleoprotein of adenovions 2. The conditions, under which the enzymatic deprotections proceed, are so mild that no undesired side reaction is observed, that is no depurination or beta elimination of the nucleosides occurs. In addition, the specificity of the biocatalysts ensures that the peptide bonds and the other protecting groups present are not attacked either.
• US4111933A
  申请人：——

  公开号：US4111933A

  公开（公告）日：1978-09-05
• Protection of functional groups during reaction and their subsequent
  申请人：Bayer Aktiengesellschaft

  公开号：US04111933A1

  公开（公告）日：1978-09-05

  In the process for preparing an organic compound of the formula A' -- X in which X is an amino group, a hydroxyl group or a carboxyl group, and A' is the remainder of the molecule, from an organic compound of the formula A -- X in which A is the remainder of the molecule which can undergo reaction to form A', by converting A -- X into a compound of the formula A -- Z -- COOR in which Z is --NH--, --O-- or a direct C--C bond, and R is a radical of the formula ##STR1## IN WHICH Y is a direct C--C single bond, the --CH.dbd.CH-- group or an arylene group, R.sup.1 to R.sup.4 each independently is hydrogen, halogen or an alkyl, aryl, aralkyl, alkoxycarbonyl, alkylaminocarbonyl, arylaminocarbonyl or cycloalkylaminocarbonyl radical, or R.sup.1 + r.sup.2 and R.sup.3 + R.sup.4 each independently completes a 5- or 6-membered carbocyclic ring, or R.sup.1 and R.sup.3 conjointly with the grouping --C--Y--C-- forms a carbocyclic ring with 5 or 6 carbon atoms, and Hal is halogen, Thereby to protect X, then converting A -- Z -- COOR into a compound of the formula A' -- Z -- COOR and then treating the compound A' -- Z -- COOR to restore the group X, the improvement which comprises effecting the treatment of the compound A' -- Z -- COOR with an alkali metal compound of a complex of monovalent cobalt. The process is applicable particularly to aminocarboxylic acids including intermediates from various stages of the synthesis of penicillins and cephalosporins.

  在制备具有公式A' -- X的有机化合物的过程中，其中X是氨基、羟基或羧基，而A'是分子的剩余部分，从具有公式A -- X的有机化合物开始，其中A是可以发生反应形成A'的分子的剩余部分，通过将A -- X转化为具有公式A -- Z -- COOR的化合物，其中Z是--NH--、--O--或直接的C--C键，R是具有##STR1##的基团，其中Y是直接的C--C单键，--CH.dbd.CH--基团或芳基基团，R.sup.1到R.sup.4各自独立地是氢、卤素或烷基、芳基、芳基烷基、烷氧羰基、烷基氨基羰基、芳基氨基羰基或环烷基氨基羰基基团，或R.sup.1 + r.sup.2和R.sup.3 + R.sup.4各自独立地完成一个5-或6-成员的碳环，或R.sup.1和R.sup.3与基团--C--Y--C--共同形成具有5或6个碳原子的碳环，Hal是卤素，从而保护X，然后将A -- Z -- COOR转化为具有公式A' -- Z -- COOR的化合物，然后处理化合物A' -- Z -- COOR以恢复基团X，改进包括使用一价钴络合物的碱金属化合物对化合物A' -- Z -- COOR进行处理。该过程特别适用于氨基羧酸，包括青霉素和头孢菌素合成各阶段的中间体。
• Design, synthesis and evaluation of novel scutellarin and scutellarein-N,N-bis-substituted carbamate-l-amino acid derivatives as potential multifunctional therapeutics for Alzheimer’s disease
  作者：Dirong Wu、Jiao Chen、Keke Luo、Hui Li、Ting Liu、Li Li、Zeqin Dai、Yongjun Li、Yonglong Zhao、Xiaozhong Fu

  DOI：10.1016/j.bioorg.2022.105760

  日期：2022.5