(S)-(-)-1-tert-butyl-2-<(tert-butoxycarbonyl)amino>-5-hexenoate | 145037-74-7

• 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: (S)-(-)-1-tert-butyl-2-<(tert-butoxycarbonyl)amino>-5-hexenoate
• 英文别名: 1-tert-butyl (2S)-tert-butoxycarbonylaminohex-5-enoate；Boc-homoallyl-Gly-OtBu；tert-butyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]hex-5-enoate
• CAS: 145037-74-7
• 化学式: C₁₅H₂₇NO₄
• 分子量: 285.384
• InChiKey: HCCCYDLUFISNCU-NSHDSACASA-N

物化性质

• 沸点：
  371.1±42.0 °C(Predicted)
• 密度：
  0.992±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  (S)-(-)-1-tert-butyl-2-<(tert-butoxycarbonyl)amino>-5-hexenoate 在 盐酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 生成 Boc-L-高烯丙基甘氨酸
  参考文献：
  名称：

  Synthesis of 5/7-, 5/8- and 5/9-bicyclic lactam templates as constraints for external β-turns

  摘要：

  5/7、5/8 和 5/9 的双环内酯 3、17、5 和 6 已通过环闭合烯烃复分解反应合成为单一的非对映体异构体。氨基酸盐酸盐 17 的 X 射线晶体结构已被测定，并与饱和外部 β-转角约束 18 的结构进行了比较。

  DOI：

  10.1039/b503014e
• 作为产物：
  描述：

  Boc-L-谷氨酸-1-叔丁酯 在 盐酸 、 tris(tert-butoxy)lithium aluminum hydride 、 双(三甲基硅烷基)氨基钾 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.0h， 生成 (S)-(-)-1-tert-butyl-2-<(tert-butoxycarbonyl)amino>-5-hexenoate
  参考文献：
  名称：

  烯丙基和高烯丙基甘氨酸的立体选择性合成

  摘要：

  从天冬氨酸和谷氨酸衍生物开发了一种新的合成N-保护的烯丙基和高烯丙基甘氨酸的方法。天冬氨酸和谷氨酸衍生物的羧基侧链首先通过与N，O-二甲基羟胺偶联而转化为Weinreb酰胺，然后还原为相应的醛。后者可以与甲基三苯基溴化react反应，以总收率50％得到标题化合物。

  DOI：

  10.1016/s0040-4039(01)00459-2

文献信息

• Design and synthesis of novel FKBP inhibitors
  作者：James R. Hauske、Peter Dorff、Susan Julin、Joseph DiBrino、Robin Spencer、Rebecca Williams

  DOI：10.1021/jm00101a005

  日期：1992.11

  Small molecule FKBP inhibitors were prepared with inhibitory activity ranging from micromolar to nanomolar. The design of these inhibitors derives from a structural analysis of the substrates for FKBP and cyclophilin. As a consequence of this analysis two key observations were made, namely: (1) amino ketone moieties are suitable as FKBP recognition elements at the P1-P1' site and (2) the P3'-P4' site will accept a trans-olefin as a suitable mimetic of a peptide moiety. The preparation of these non-peptide inhibitors is readily accomplished by a protocol which includes the synthesis of chiral propargylic amines and their subsequent conversion into vinyl zirconium reagents.
• Collagen cross-links: a convenient synthesis of tert-butyl-(2S)-2-[(tert-butoxycarbonyl)amino]-4-(2-oxiranyl)butanoate
  作者：Maciej Adamczyk、Donald D Johnson、Rajarathnam E Reddy

  DOI：10.1016/s0957-4166(99)00055-5

  日期：1999.2

  An efficient synthesis of tert-butyl-(2S)-2-[(tert-butoxycarbonyl)amino]-4-(2-oxiranyl)butanoate (5), the key intermediate for preparation of collagen cross-links (+)-pyridinoline (Pyd, 1) and (+)-deoxypyridinoline (Dpd, 2) was described from (4S)-5-(tert-butoxy)-4-[(tert-butoxycarbonyl)amino]-5-oxopentanoic acid (6) in six steps. Also, an improved synthesis of iodide (2S)-(-)-4b was presented. (C) 1999 Elsevier Science Ltd. All rights reserved.
• First total synthesis of the bone resorption markers deoxypyridinoline and hydroxypyridinoline
  作者：Rudolf Waelchli、Ch Beerli、H Meigel、L Révész

  DOI：10.1016/s0960-894x(97)10084-1

  日期：1997.11

  The first total synthesis of the collagen crosslinks deoxypyridinoline 1 and hydroxypyridinoline 2 was achieved. The key intermediate, pyridine 3 served as starting material for the preparation of compounds 1 and 2 and derivatives of 1. These compounds create optimal tools to establish a diagnostic kit for bone resorption. (C) 1997 Elsevier Science Ltd.
• Synthesis of 5/7-, 5/8- and 5/9-bicyclic lactam templates as constraints for external β-turns
  作者：Heather M. E. Duggan、Peter B. Hitchcock、Douglas W. Young

  DOI：10.1039/b503014e

  日期：——

  The 5/7-, 5/8- and 5/9-bicyclic lactams 3, 17, 5 and 6 have been synthesised as single diastereoisomers by a route involving ring closing olefin metathesis. The X-ray crystal structure of the amino acid hydrochloride 17 has been carried out and compared to that of the saturated external β-turn constraint 18.

  5/7、5/8 和 5/9 的双环内酯 3、17、5 和 6 已通过环闭合烯烃复分解反应合成为单一的非对映体异构体。氨基酸盐酸盐 17 的 X 射线晶体结构已被测定，并与饱和外部 β-转角约束 18 的结构进行了比较。
• Stereoselective synthesis of allyl- and homoallylglycines
  作者：Céline Douat、Annie Heitz、Jean Martinez、Jean-Alain Fehrentz

  DOI：10.1016/s0040-4039(01)00459-2

  日期：2001.5

  A new method for the synthesis of N-protected allyl- and homoallylglycines was developed from aspartic and glutamic acid derivatives. The carboxylic side-chains of aspartic and glutamic derivatives was first transformed into the Weinreb amide by coupling with N,O-dimethylhydroxylamine and then reduced into the corresponding aldehyde. The latter could react with methyl-triphenylphosphonium bromide to

  从天冬氨酸和谷氨酸衍生物开发了一种新的合成N-保护的烯丙基和高烯丙基甘氨酸的方法。天冬氨酸和谷氨酸衍生物的羧基侧链首先通过与N，O-二甲基羟胺偶联而转化为Weinreb酰胺，然后还原为相应的醛。后者可以与甲基三苯基溴化react反应，以总收率50％得到标题化合物。