Fmoc-DiMeGln | 863766-46-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-DiMeGln
• 英文别名: Nα-Fmoc-(2S,3S,4R)-3,4-dimethylglutamine；(2S,3S,4R)-Fmoc-diMeGln-OH；(2S,3S,4R)-5-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3,4-dimethyl-5-oxopentanoic acid
• CAS: 863766-46-5
• 化学式: C₂₂H₂₄N₂O₅
• 分子量: 396.443
• InChiKey: JKOVVBAZBYDBAC-QUJCMNEKSA-N

物化性质

• 熔点：
  210 °C (decomp)
• 沸点：
  691.1±55.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Fmoc-DiMeGln 、 (2R,3R,4S)-2O,3O-benzylidene-4-(9-fluorenylmethoxycarbonyl)amino-7-[N,N'-bis(benzyloxycarbonyl)guanidino]-2,3-dihyedoxyheptanoic acid 、 Fmoc-D-丙氨酸 、 芴甲氧羰基-L-苏氨酸 以35%的产率得到callipeltin D
  参考文献：
  名称：

  Callipeltin D的固相合成。立体化学证实了非天然氨基酸AGDHE。

  摘要：

  [结构：参见正文]使用基于Fmoc的固相策略以七个步骤和35％的总收率合成了脂肽Callipeltin D（1）。合成1的1H NMR与天然产物的1H NMR密切相关，确认了新型氨基酸成分（2R，3R，4S）-4-氨基-7-胍基-2,3-二羟基庚酸的构型分配。

  DOI：

  10.1021/ol052438f
• 作为产物：
  描述：

  tert-butyl N-Boc-(2S,3S,4R)-3,4-dimethylpyroglutamate 在 europium(III) trifluoroacetate 、 氨 、 二甲基氯化铝 、 三氟乙酸 、 lithium hexamethyldisilazane 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 Fmoc-DiMeGln
  参考文献：
  名称：

  Synthesis of N-Fmoc-(2S,3S,4R)-3,4-dimethylglutamine: An Application of Lanthanide-Catalyzed Transamidation

  摘要：

  N-Fmoc-(2S,3S,4R)-3,4-dimethylglutamine (6) was synthesized from tert-butyl N-Boc-(2S,3S,4R)dimethylpyroglutamate (13). This synthesis involved selective deprotection of a Boc group from a lactam nitrogen in the presence of a tert-butyl ester, Fmoc protection of the lactam, and a lanthanidecatalyzed transamidation reaction of the Fmoc-protected lactam, using ammonia and dimethylaluminum chloride. The scope of Lewis acid-catalyzed transamidation of acylated lactams was explored through the variation of lanthanide, lactam, acyl group, amine, and aluminum reagent. The reactivity of various metal triflates was found to vary in the following qualitative order: Yb Sc > Er similar to Eu similar to Sm > Ce similar to Agl > Cu-II similar to Zn. Intriguingly, catalysis was only observed when ammonia was the nitrogen nucleophile; addition of other amidoaluminum complexes to acyl lactams was found to be insensitive to the addition of lanthanides.

  DOI：

  10.1021/jo050518r

文献信息

• [EN] SYNTHETIC PROCESS FOR THE MANUFACTURE OF PIPECOLIDEPSIN COMPOUNDS<br/>[FR] PROCÉDÉ DE SYNTHÈSE POUR LA FABRICATION DE COMPOSÉS DE PIPÉCOLIDEPSINE
  申请人：PHARMA MAR SA

  公开号：WO2014108526A1

  公开（公告）日：2014-07-17

  (I) wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, n and Y are as described. The invention provides a process for the synthesis of complex pipecolidepsin and related compounds of formula (I), opening a new field of compounds with useful biological properties. The invention also provides intermediates, useful in the synthesis of compounds of formula (I).
• Solid-Phase Synthesis of Callipeltin D. Stereochemical Confirmation of the Unnatural Amino Acid AGDHE
  作者：David C. Cranfill、Ángel I. Morales-Ramos、Mark A. Lipton

  DOI：10.1021/ol052438f

  日期：2005.12.1

  [structure: see text] The lipopeptide callipeltin D (1) was synthesized using an Fmoc-based solid-phase strategy in seven steps and 35% overall yield. The 1H NMR of synthetic 1 correlated closely with that of the natural product, confirming the configurational assignment of the novel amino acid constituent (2R,3R,4S)-4-amino-7-guanidino-2,3-dihydroxyheptanoic acid.

  [结构：参见正文]使用基于Fmoc的固相策略以七个步骤和35％的总收率合成了脂肽Callipeltin D（1）。合成1的1H NMR与天然产物的1H NMR密切相关，确认了新型氨基酸成分（2R，3R，4S）-4-氨基-7-胍基-2,3-二羟基庚酸的构型分配。
• Synthesis of <i>N</i>-Fmoc-(2<i>S</i>,3<i>S</i>,4<i>R</i>)-3,4-dimethylglutamine: An Application of Lanthanide-Catalyzed Transamidation
  作者：Selçuk Çalimsiz、Mark A. Lipton

  DOI：10.1021/jo050518r

  日期：2005.8.1

  N-Fmoc-(2S,3S,4R)-3,4-dimethylglutamine (6) was synthesized from tert-butyl N-Boc-(2S,3S,4R)dimethylpyroglutamate (13). This synthesis involved selective deprotection of a Boc group from a lactam nitrogen in the presence of a tert-butyl ester, Fmoc protection of the lactam, and a lanthanidecatalyzed transamidation reaction of the Fmoc-protected lactam, using ammonia and dimethylaluminum chloride. The scope of Lewis acid-catalyzed transamidation of acylated lactams was explored through the variation of lanthanide, lactam, acyl group, amine, and aluminum reagent. The reactivity of various metal triflates was found to vary in the following qualitative order: Yb Sc > Er similar to Eu similar to Sm > Ce similar to Agl > Cu-II similar to Zn. Intriguingly, catalysis was only observed when ammonia was the nitrogen nucleophile; addition of other amidoaluminum complexes to acyl lactams was found to be insensitive to the addition of lanthanides.