(2R,3S)-2-(N-carbobenzoxy)amino-1,1,1-trifluoro-hex-5-en-3-ol | 219953-66-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S)-2-(N-carbobenzoxy)amino-1,1,1-trifluoro-hex-5-en-3-ol
• 英文别名: benzyl N-[(2R,3S)-1,1,1-trifluoro-3-hydroxyhex-5-en-2-yl]carbamate
• CAS: 219953-66-9
• 化学式: C₁₄H₁₆F₃NO₃
• 分子量: 303.281
• InChiKey: MKUBBUHFSIKKLZ-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-(N-carbobenzoxy)amino-1,1,1-trifluoro-hex-5-en-3-ol 在 potassium permanganate 、 硫酸 作用下， 以 水 、 丙酮 为溶剂， 反应 0.08h， 以70%的产率得到4-(N-carbobenzoxy)amino-3-hydroxy-5,5,5-trifluoropentanoic acid
  参考文献：
  名称：

  包含两个三氟甲基羟亚甲基等排体（Tfm-GABOB）的胃抑素类似物的全合成和含Tfm-GABOB的肽作为HIV-1蛋白酶和MMP-9抑制剂的评估

  摘要：

  我们描述了天冬氨酸蛋白酶抑制剂胃抑素的三氟甲基（Tfm）类似物的不对称总合成，该蛋白结合了两个γ-Tfm-γ-氨基-β-羟基丁酸（γ-Tfm-GABOB）单元而不是天然他汀类单元。测试了标题化合物以及几种Tfm取代的前体作为HIV-1蛋白酶和明胶酶B（MMP-9）的抑制剂

  DOI：

  10.1016/s0040-4020(01)00543-9
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 以94%的产率得到(2R,3S)-2-(N-carbobenzoxy)amino-1,1,1-trifluoro-hex-5-en-3-ol
  参考文献：
  名称：

  包含两个三氟甲基羟亚甲基等排体（Tfm-GABOB）的胃抑素类似物的全合成和含Tfm-GABOB的肽作为HIV-1蛋白酶和MMP-9抑制剂的评估

  摘要：

  我们描述了天冬氨酸蛋白酶抑制剂胃抑素的三氟甲基（Tfm）类似物的不对称总合成，该蛋白结合了两个γ-Tfm-γ-氨基-β-羟基丁酸（γ-Tfm-GABOB）单元而不是天然他汀类单元。测试了标题化合物以及几种Tfm取代的前体作为HIV-1蛋白酶和明胶酶B（MMP-9）的抑制剂

  DOI：

  10.1016/s0040-4020(01)00543-9

文献信息

• Stereocontrolled approaches to (+)- and (−)-γ-trifluoromethyl-GABOB, a new hydroxymethylene (statine) dipeptide isostere
  作者：Pierfrancesco Bravo、Eleonora Corradi、Cristina Pesenti、Barbara Vergani、Fiorenza Viani、Alessandro Volonterio、Matteo Zanda

  DOI：10.1016/s0957-4166(98)00397-8

  日期：1998.11

  Two efficient approaches to both enantiomers of syn-gamma-triffuoromethyl gamma-amino beta-hydroxy butyric acid (gamma-Tfm-GABOB) (10), a new hydroxymethylene (statine) dipeptide isostere, are described. One exploits the recently disclosed 'non-oxidative' Pummerer reaction, by means of which ex-lithium alkyl sulfoxides are used as chiral alpha-hydroxyalkyl anion equivalents in the synthesis of beta-amino alcohols. Trifluoropyruvaldehyde-N,S-ketal (R)-11, a novel stereochemically stable synthetic equivalent of alpha-amino trifluoropropanal, is used in the second approach. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Unusual nonchelation controlled allylation of a N -monoprotected α-amino aldehyde: stereoselective entry to nonracemic trifluoromethyl dipeptide isosteres
  作者：Alessandro Volonterio、Pierfrancesco Bravo、Eleonora Corradi、Giovanni Fronza、Stefano V Meille、Barbara Vergani、Matteo Zanda

  DOI：10.1016/s0022-1139(01)00363-3

  日期：2001.5

  An efficient synthesis of the non-racemic (66-68% e.e.) homoallylic beta -trifluoromethyl beta -amino alcohol (2S,3R)-9, a key intermediate in the synthesis of trifluoromethylated dipeptide isosteres and oligopeptides, was developed starting from N-Cbz-trifluoropyruvaldehyde-N,S-ketal (R)-1a. The correct syn-stereochemistry was achieved by combining two moderately stereoselective steps: (1) addition of allylmagnesium chloride to (R)-1a, occurring with unusual nonchelation control; (2) reductive: desulfenylation of the phenylacetate 6 with NaBH4/pyridine. (C) 2001 Elsevier Science B.V. All rights reserved.
• Total synthesis of a Pepstatin analogue incorporating two trifluoromethyl hydroxymethylene isosteres
  作者：Cristina Pesenti、Alberto Arnone、Anne Marie Aubertin、Pierfrancesco Bravo、Massimo Frigerio、Walter Panzeri、Sylvie Schmidt、Fiorenza Viani、Matteo Zanda

  DOI：10.1016/s0040-4039(00)01244-2

  日期：2000.9

  The total synthesis of a trifluoromethyl (Tfm) analogue of the aspartate protease inhibitor Pepstatin has been accomplished via incorporation of two alpha-Tfm-amino beta-hydroxy peptide isosteres instead of the natural statine units. The title compound as well as several Tfm-substituted precursors did not show anti-HIV activity. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Total synthesis of a pepstatin analog incorporating two trifluoromethyl hydroxymethylene isosteres (Tfm-GABOB) and evaluation of Tfm-GABOB containing peptides as inhibitors of HIV-1 protease and MMP-9
  作者：Cristina Pesenti、Alberto Arnone、Stefano Bellosta、Pierfrancesco Bravo、Monica Canavesi、Eleonora Corradi、Massimo Frigerio、Stefano V Meille、Mara Monetti、Walter Panzeri、Fiorenza Viani、Romina Venturini、Matteo Zanda

  DOI：10.1016/s0040-4020(01)00543-9

  日期：2001.7

  We describe the asymmetric total synthesis of a trifluoromethyl (Tfm) analogue of the aspartate protease inhibitor pepstatin incorporating two γ-Tfm-γ-amino-β-hydroxybutyric acid (γ-Tfm-GABOB) units instead of the natural statine units. The title compound as well as several Tfm-substituted precursors were tested as inhibitors of HIV-1 protease and Gelatinase B (MMP-9)

  我们描述了天冬氨酸蛋白酶抑制剂胃抑素的三氟甲基（Tfm）类似物的不对称总合成，该蛋白结合了两个γ-Tfm-γ-氨基-β-羟基丁酸（γ-Tfm-GABOB）单元而不是天然他汀类单元。测试了标题化合物以及几种Tfm取代的前体作为HIV-1蛋白酶和明胶酶B（MMP-9）的抑制剂