Boc-D-Valine pentafluorophenyl ester | 182360-34-5

• 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-D-Valine pentafluorophenyl ester
• 英文别名: N-Boc-D-valine pentafluorophenyl ester；D-N-(tert-butoxycarbonyl)valine pentafluorophenyl ester；t-butoxycarbonyl-D-valine pentafluorophenyl ester；N-Boc-D-Val-OPfP；(2,3,4,5,6-pentafluorophenyl) (2R)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 182360-34-5
• 化学式: C₁₆H₁₈F₅NO₄
• 分子量: 383.315
• InChiKey: LHMQOAPYTSAHML-GFCCVEGCSA-N

物化性质

• 沸点：
  403.6±45.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Boc-D-Valine pentafluorophenyl ester 在 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 钾硼氢 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.08h， 生成 benzyl (2S)-1-[(2S)-2-[[(2S)-2-[(3S,4R)-3-hydroxy-5-methyl-4-[[(2S,3R)-3-[(2S)-2-[methyl(phenylmethoxycarbonyl)amino]-3-naphthalen-2-ylpropanoyl]oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]hexanoyl]oxy-3-methylbutanoyl]amino]-4-methylpentanoyl]pyrrolidine-2-carboxylate
  参考文献：
  名称：

  玉兰素B类似物的全合成及生物学评价

  摘要：

  丹丹素A和B是一类海洋天然环二肽，其结构和生物活性与二羟肌酐密切相关。合成的坦丹更容易获得，从而加快了该抗肿瘤，抗病毒和免疫抑制化合物家族新的大环衍生物的制备。通过将大内酰胺化位点从Nst 1和Thr 6更改为Pro 4和N，O -Me 2 Tyr 5来优化先前报道的合成坦丹林的合成路线残留物导致反应产率的显着提高。使用这种新的合成方法，制备了tamandarin B的四个新的大环类似物，并评估了其抗癌活性。这些结果提供了进一步的见解，其坦丹林和双精胺的结构活性关系。

  DOI：

  10.1021/jo070412r
• 作为产物：
  描述：

  D-缬氨酸 在 吡啶 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 Boc-D-Valine pentafluorophenyl ester
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Tamandarin B Analogues

  摘要：

  [GRAPHICS]The synthesis of two tamandarin B analogues in which the N,O-Me(2)Tyr(5) unit was replaced by N-Me-phenylaianine (N-MePhe(5)) and (S)-2(methylamino)-3-(naphthalen-2-yl)propanoic acid (N-MeNaphth(5)) is described. The choice of the macrocyclization site was crucial to achieve satisfactory macrolactamization. Coupling between norstatine (Nst(1)) and threonine (Thr(6)) afforded only a 15% yield, while lactamization between proline (Pro(4)) and the aromatic moiety could be achieved in 65% yield.

  DOI：

  10.1021/ol0530023

文献信息

• Total Synthesis of (−)-Muscoride A
  作者：Peter Wipf、Srikanth Venkatraman

  DOI：10.1021/jo960891m

  日期：1996.1.1

  the presence of a threonine-derived bioxazole core and an N-(1,1-dimethyl)allyl ("reverse prenyl") valine residue. In the context of our synthesis, efficient new strategies for the preparation of these segments were developed. The synthesis of two epimers of muscoride A allowed the unambiguous assignment of the relative and absolute configuration of the natural product by NMR and optical rotation analyses

  15步合成了最近分离的蓝藻代谢产物muscoride A，总产率为4.3％。该肽抗生素的新结构特征包括苏氨酸衍生的生物恶唑核和N-（1，1-二甲基）烯丙基（“反向异戊烯基”）缬氨酸残基的存在。在我们的综合背景下，开发了用于制备这些片段的有效新策略。粘胶A的两个差向异构体的合成允许通过NMR和旋光分析明确分配天然产物的相对和绝对构型。
• The first enantioselective synthesis of cytotoxic marine natural product palau’imide and assignment of its C-20 stereochemistry
  作者：Hong-Qiao Lan、Yuan-Ping Ruan、Pei-Qiang Huang

  DOI：10.1039/c0cc00452a

  日期：——

  racemization-free synthesis of methyl 5-benzyl-3-methyltetramate via alkylation, and used in the first asymmetric synthesis of palau'imide (1). This allowed the establishment of the hitherto unknown stereochemistry at the C-20 of palau'imide as S.

  四甲基丙烯酸甲酯衍生物6已被开发为通过烷基化灵活，无消旋地合成5-苄基-3-甲基四甲基丙烯酸甲酯的新组成部分，并被用于首次合成不对称的palau'imide（1）。这使得迄今为止在帕劳酰亚胺的C-20上建立了迄今未知的立体化学S。
• Total Synthesis of Spiruchostatin A, a Potent Histone Deacetylase Inhibitor
  作者：Alexander Yurek-George、Fay Habens、Matthew Brimmell、Graham Packham、A. Ganesan

  DOI：10.1021/ja039258q

  日期：2004.2.1

  The total synthesis of spiruchostatin A was accomplished, unambiguously confirming its structure. Key steps included the use of the Nagao thiazolidinethione auxiliary for a diastereoselective acetate aldol reaction and as an activated acylating agent for amide formation, and macrolactonization by the Yamaguchi protocol. Spiruchostatin A is shown to have biological activity similar to that of FK228, a potent histone deacetylase (HDAC) inhibitor in clinical trials. The spiruchostatin A analogue, epimeric at the beta-hydroxy acid, is inactive, highlighting the importance of stereochemistry at this position for interactions with HDACs.
• An efficient synthesis of the tamandarin B macrocycle
  作者：Kenneth M. Lassen、Jisun Lee、Madeleine M. Joullié

  DOI：10.1016/j.tetlet.2009.12.091

  日期：2010.3

  A reliable, high yielding cyclization protocol for the macrocycle of tamandarin B is presented. This strategy will facilitate the synthesis of side chain analogs. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of Tamandarin B Analogues
  作者：Javier Adrio、Carmen Cuevas、Ignacio Manzanares、Madeleine M. Joullié

  DOI：10.1021/ol0530023

  日期：2006.2.1

  [GRAPHICS]The synthesis of two tamandarin B analogues in which the N,O-Me(2)Tyr(5) unit was replaced by N-Me-phenylaianine (N-MePhe(5)) and (S)-2(methylamino)-3-(naphthalen-2-yl)propanoic acid (N-MeNaphth(5)) is described. The choice of the macrocyclization site was crucial to achieve satisfactory macrolactamization. Coupling between norstatine (Nst(1)) and threonine (Thr(6)) afforded only a 15% yield, while lactamization between proline (Pro(4)) and the aromatic moiety could be achieved in 65% yield.