Benzyl 2(S)-<(tert-butoxycarbonyl)amino>-3-cyanopropionate | 95407-39-9

• 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: Benzyl 2(S)-<(tert-butoxycarbonyl)amino>-3-cyanopropionate
• 英文别名: N-(tert-butoxycarbonyl)-3-cyanoalanine benzyl ester；(S)-benzyl 2-((tert-butoxycarbonyl)amino)-3-cyanopropanoate；benzyl (2S)-3-cyano-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 95407-39-9
• 化学式: C₁₆H₂₀N₂O₄
• 分子量: 304.346
• InChiKey: WKUAXNOREZLBIC-ZDUSSCGKSA-N

物化性质

• 沸点：
  481.4±45.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  88.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Benzyl 2(S)-<(tert-butoxycarbonyl)amino>-3-cyanopropionate 在 水 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 3-cyanoalanine benzyl ester
  参考文献：
  名称：

  Synthesis of optically pure pipecolates from L-asparagine. Application to the total synthesis of (+)-apovincamine through amino acid decarbonylation and iminium ion cyclization

  摘要：

  DOI：

  10.1021/jo00208a017
• 作为产物：
  描述：

  BOC-L-天冬酰胺 在 吡啶 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 50.0h， 生成 Benzyl 2(S)-<(tert-butoxycarbonyl)amino>-3-cyanopropionate
  参考文献：
  名称：

  Synthesis of optically pure pipecolates from L-asparagine. Application to the total synthesis of (+)-apovincamine through amino acid decarbonylation and iminium ion cyclization

  摘要：

  DOI：

  10.1021/jo00208a017

文献信息

• Antiherpes pentapeptides
  申请人：BIO-MEGA/BOEHRINGER INGELHEIM RESEARCH INC.

  公开号：EP0408973A1

  公开（公告）日：1991-01-23

  Disclosed herein are pentapeptide derivatives of the formula XNR¹-CH(R²)-C(O)-NH-CH(R³)-C(O)-NR⁴-CH(CH₂Y)-CO-­NH-CH[CR⁵(R⁶)-COOH]-C(W)-NH-CH(R⁷)-Z wherein X is a terminal group, for example, alkanoyl or phenylalkanoyl radicals, R¹ is alkyl or phenylalkyl, R², R³ and R⁷ are selected from the side chains of amino acid or derived amino acid residues, R⁴, R⁵, and R⁶ are hydrogen or lower alkyl, W is oxo or thioxo, Y is carboxy, carbamyl or 5-1H-tetrazolyl and Z is carboxy or 5-1H-tetrazolyl. The derivatives are useful for treating herpes infections.

  本文公开了式 XNR¹-CH(R²)-C(O)-NH-CH(R³)-C(O)-NR⁴-CH(CH₂Y)-CO-NH-CH[CR⁵(R⁶)-COOH]-C(W)-NH-CH(R⁷)-Z 的五肽衍生物，其中 X 是末端基团、例如烷酰基或苯基烷酰基，R¹ 是烷基或苯基烷基、R²、R³ 和 R⁷ 选自氨基酸或衍生氨基酸残基的侧链，R⁴、R⁵ 和 R⁶ 是氢或低级烷基，W 是氧代或硫代，Y 是羧基、氨基甲酰基或 5-1H- 四唑基，Z 是羧基或 5-1H- 四唑基。这些衍生物可用于治疗疱疹感染。
• Synthesis of Enantiomerically Pure Unsaturated .alpha.-Amino Acids Using Serine-Derived Zinc/Copper Reagents
  作者：Michael J. Dunn、Richard F. W. Jackson、Joerg Pietruszka、Debra Turner

  DOI：10.1021/jo00112a048

  日期：1995.4

  Treatment of the serine-derived organozinc reagent 2, in benzene/dimethylacetamide, with a THF solution of CuCN . 2LiCl gives rise to a zinc/copper reagent 6 which reacts directly with allylic halides and tosylates to give the corresponding enantiomerically pure substitution products 9 in 32-65% yield (11 examples). The reaction proceeds by formal S(N)2' displacement of the leaving group. Reaction with propargyl halides gives the corresponding terminal allene 12a. The zinc reagent 2 may also be prepared directly from protected iodoalanine 1 in THP by the Knochel method. Reaction with propargylic tosylates as electrophiles gives rise to the corresponding protected terminal allenic amino acids in 51-81% yield (four examples); use of enantiomerically enriched propargylic tosylates results in the formation of diastereoisomerically enriched allenic products. Reactions of the zinc/copper reagent 6 with a range of representative electrophiles is explored; use of relatively reactive electrophiles is necessary to obtain satisfactory yields. Finally, the possibility of using the serine-derived iodide 20, in which the carboxylic acid is protected as a methyl ester, is established: This reagent offers advantages over the corresponding benzyl ester protected reagent 6 for the synthesis of unsaturated amino acids.
• An Improved Synthesis of β-Cyano-l-Alanine Esters and Amides
  作者：Guoxin Wang、Zigang Li、Longjian Chen、Xiaodan Cai、Ming Luo

  DOI：10.1055/s-0035-1560489

  日期：——

  We have developed a novel, mild, efficient, and scalable protocol for the synthesis of N-protected -cyano-l-alanine esters or amides from N-protected l-asparagin. This protocol avoided the use of toxic or unpleasant reagents and was easy to operate in laboratory.
• BALDWIN, JACK E.;BRADLEY, MARK;ABBOTT, SHAUN D.;ADLINGTON, R. M., J. CHEM. SOC. CHEM. COMMUN.,(1990) N5, C. 1008-1010
  作者：BALDWIN, JACK E.、BRADLEY, MARK、ABBOTT, SHAUN D.、ADLINGTON, R. M.

  DOI：——

  日期：——
• US5648337A
  申请人：——

  公开号：US5648337A

  公开（公告）日：1997-07-15