4-fluoro-5,5'-dihydroxy-leucine | 133384-70-0

• 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: 4-fluoro-5,5'-dihydroxy-leucine
• 英文别名: 2-Amino-4-fluoro-5-hydroxy-4-(hydroxymethyl)pentanoic acid
• CAS: 133384-70-0
• 化学式: C₆H₁₂FNO₄
• 分子量: 181.164
• InChiKey: GVDYVPBWNHZUND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  104
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-fluoro-5,5'-dihydroxy-leucine 在 吡啶 作用下， 以 甲醇 为溶剂， 反应 21.0h， 生成 (2S4S, 2R4R) 3-acetamido-5-fluoro-5-(acetoxymethyl)tetrahydropyran-2-one
  参考文献：
  名称：

  Dugave, C.; Dubois, J.; Bory, S., Bulletin de la Societe Chimique de France, 1991, # 3, p. 381 - 386

  摘要：

  DOI：
• 作为产物：
  描述：

  N-phthalyl-4-fluoro-4-benzyloxycarbonyl-glutamic acid, α-methyl, γ-benzyl diester 在 palladium on activated charcoal 盐酸 、 dimethyl sulfide borane 、 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 5.5h， 生成 4-fluoro-5,5'-dihydroxy-leucine
  参考文献：
  名称：

  Synthesis of 5,5′-dihydroxyleucine and 4-fluoro 5,5′-dihydroxyleucine, the reduction products of 4-carboxyglutamic and 4-carboxy-4-fluoroglutamic acids

  摘要：

  Schemes for the synthesis of 5-5'-dihydroxyleucine 3 and its 4-fluoro analog 7 involving the condensation of a suitable ''aminoacid moiety'' with 2,2-dimethyl-5-iodomethyl-1,3-dioxane 15D or its fluoro analog 27A were tested. The anion of the ethyl N-diphenylmethylene-glycinate 25 gave better yields of 3 than the classical anion of diethyl acetamidomalonate. This strategy could not be successfully applied to the synthesis of 7, which could be prepared by reduction of a suitably protected 4-fluoro-4-carboxyglutamate with BMS.

  DOI：

  10.1016/s0040-4020(01)80939-x

文献信息

• Synthesis of 5,5′-dihydroxyleucine and 4-fluoro 5,5′-dihydroxyleucine, the reduction products of 4-carboxyglutamic and 4-carboxy-4-fluoroglutamic acids
  作者：Joëlle Dubois、Christine Fourès、Sonia Bory、Serge Falcou、Michel Gaudry、Andrée Marquet

  DOI：10.1016/s0040-4020(01)80939-x

  日期：1991.1

  Schemes for the synthesis of 5-5'-dihydroxyleucine 3 and its 4-fluoro analog 7 involving the condensation of a suitable ''aminoacid moiety'' with 2,2-dimethyl-5-iodomethyl-1,3-dioxane 15D or its fluoro analog 27A were tested. The anion of the ethyl N-diphenylmethylene-glycinate 25 gave better yields of 3 than the classical anion of diethyl acetamidomalonate. This strategy could not be successfully applied to the synthesis of 7, which could be prepared by reduction of a suitably protected 4-fluoro-4-carboxyglutamate with BMS.
• Dugave, C.; Dubois, J.; Bory, S., Bulletin de la Societe Chimique de France, 1991, # 3, p. 381 - 386
  作者：Dugave, C.、Dubois, J.、Bory, S.、Gaudry, M.、Marquet, A.

  DOI：——

  日期：——