(2S,5S,1'S)-5-{1'-[(tert-butoxycarbonyl)amino]ethyl}tetrahydrofuran-2-carboxylic acid | 259091-41-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (2S,5S,1'S)-5-{1'-[(tert-butoxycarbonyl)amino]ethyl}tetrahydrofuran-2-carboxylic acid
• 英文别名: (2S,5S)-5-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]oxolane-2-carboxylic acid
• CAS: 259091-41-3
• 化学式: C₁₂H₂₁NO₅
• 分子量: 259.302
• InChiKey: OESPOHHPFMGZPY-CIUDSAMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,5S,1'S)-5-{1'-[(tert-butoxycarbonyl)amino]ethyl}tetrahydrofuran-2-carboxylic acid 在 lithium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.33h， 生成
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Integrin Antagonists Containingtrans- andcis-2,5-Disubstituted THF Rings

  摘要：

  The synthesis of a series of RGD mimetics is described. All compounds consist of a central 2,5-disubstituted tetrahydrofuran core, a variable linker to a guanidino group, and a beta-amino alanine unit to mimic the carboxylic acid. Three types of linkers were investigated: a simple four-atom methylene chain (type A, compounds 14, 15, 16, and 17), a four-atom methylene chain with an additional chiral center, and a nitrogen substituent (type B, compounds 38, 39, and 40), and an amide linker of different length with an additional chiral center (type C, compounds 59, 60, 61 and 62). A variety of compounds were tested as potential integrin antagonists in a receptor binding assay (alpha(IIb)beta(3), alpha(v)beta(3), and alpha(v)beta(5)). The relative and absolute configuration of the chiral centers at the THF ring had a pronounced effect on the binding activity and selectivity Compound 14 proved to be a selective inhibitor of to be a selective inhibitor of to be a selective inhibitor of alpha(IIb)beta(3) (IC50 = 20nM), whereas compound 40 exhibited high activity for binding of alpha(IIb)beta(3) (IC50 = 67 nM) and alpha(v)beta(3) (IC50 = 52 nM).

  DOI：

  10.1002/(sici)1521-3765(20000218)6:4<666::aid-chem666>3.0.co;2-z
• 作为产物：
  描述：

  (3S,4S)-4-Dibenzylamino-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-1-yn-3-ol 在 palladium dihydroxide 吡啶 、 pyridine-SO3 complex 、 camphor-10-sulfonic acid 、 氢气 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (2S,5S,1'S)-5-{1'-[(tert-butoxycarbonyl)amino]ethyl}tetrahydrofuran-2-carboxylic acid
  参考文献：
  名称：

  立体选择合成3,4-二脱氧呋喃糖氨基酸的各种异构体，在C6位进行甲基取代

  摘要：

  按照共同的策略合成了各种含C6-甲基的手性3,4-二脱氧呋喃糖氨基酸异构体，其中C2和C6的手性中心来源于两种原料的手性：甘油醛丙酮化物和N，N -二苄基丙氨酸分别通过标准的非对映选择性转化固定C5中心。

  DOI：

  10.1016/j.tetlet.2005.04.094

文献信息

• Synthesis of Enantiomerically Pure Amino Acids Containing 2,5-Disubstituted THF Rings in the Molecular Backbone
  作者：Anna Schrey、Frank Osterkamp、Alrun Straudi、Corry Rickert、Holger Wagner、Ulrich Koert、Bernhard Herrschaft、Klaus Harms

  DOI：10.1002/(sici)1099-0690(199911)1999:11<2977::aid-ejoc2977>3.0.co;2-3

  日期：1999.11

  N- and C-protected derivatives of 2,5-disubstituted trans- and cis-THF amino acids 6 and 7 were prepared in enantiomerically pure form from L-alanine. Felkin–Anh-controlled reduction of the ketone 9 was achieved with a 85:15 diastereoselectivity. Epoxidation of 10 and subsequent intramolecular epoxide opening gave the trans- and cis-THF alcohols 11 and 12, which were further transformed into the corresponding

  ñ -和C ^ -保护的衍生物2,5-二取代反式-和顺-THF氨基酸6和7中，从L-丙氨酸对映体纯形式制备。用Felkin-Anh控制的酮9的还原反应非对映选择性为85:15。环氧化反应的10和随后的分子内环氧化物开环得到反式-和顺-THF醇11和12，这是进一步转化为相应的Ñ -和C ^ -保护的2,5-二取代反式-和顺式-THF氨基酸。构象研究表明，顺式-THF二酰胺34在固态和CDCl 3溶液中为β-转弯模拟物。
• Stereoselective synthesis of the various isomers of 3,4-dideoxy furanoid sugar amino acids with methyl substitution at the C6 position
  作者：Tushar Kanti Chakraborty、Gangarajula Sudhakar

  DOI：10.1016/j.tetlet.2005.04.094

  日期：2005.6

  Various isomers of C6-methyl-containing chiral 3,4-dideoxy furanoid sugar amino acids were synthesized following a common strategy, in which the C2 and C6 chiral centres were derived from the chiralities of the two starting materials, glyceraldehyde acetonide and N,N-dibenzylalaninal, respectively, and the C5 centre was fixed by standard diastereoselective transformations.

  按照共同的策略合成了各种含C6-甲基的手性3,4-二脱氧呋喃糖氨基酸异构体，其中C2和C6的手性中心来源于两种原料的手性：甘油醛丙酮化物和N，N -二苄基丙氨酸分别通过标准的非对映选择性转化固定C5中心。
• Synthesis and Biological Evaluation of Integrin Antagonists Containingtrans- andcis-2,5-Disubstituted THF Rings
  作者：Frank Osterkamp、Burkhard Ziemer、Ulrich Koert、Matthias Wiesner、Peter Raddatz、Simon L. Goodman

  DOI：10.1002/(sici)1521-3765(20000218)6:4<666::aid-chem666>3.0.co;2-z

  日期：2000.2.18

  The synthesis of a series of RGD mimetics is described. All compounds consist of a central 2,5-disubstituted tetrahydrofuran core, a variable linker to a guanidino group, and a beta-amino alanine unit to mimic the carboxylic acid. Three types of linkers were investigated: a simple four-atom methylene chain (type A, compounds 14, 15, 16, and 17), a four-atom methylene chain with an additional chiral center, and a nitrogen substituent (type B, compounds 38, 39, and 40), and an amide linker of different length with an additional chiral center (type C, compounds 59, 60, 61 and 62). A variety of compounds were tested as potential integrin antagonists in a receptor binding assay (alpha(IIb)beta(3), alpha(v)beta(3), and alpha(v)beta(5)). The relative and absolute configuration of the chiral centers at the THF ring had a pronounced effect on the binding activity and selectivity Compound 14 proved to be a selective inhibitor of to be a selective inhibitor of to be a selective inhibitor of alpha(IIb)beta(3) (IC50 = 20nM), whereas compound 40 exhibited high activity for binding of alpha(IIb)beta(3) (IC50 = 67 nM) and alpha(v)beta(3) (IC50 = 52 nM).