6(S)-propyl-5,6,7,8-tetrahydropterin | 136778-66-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 6(S)-propyl-5,6,7,8-tetrahydropterin
• 英文别名: 6(s)-Propyl-tetrahydropterin；(6S)-2-amino-6-propyl-5,6,7,8-tetrahydro-3H-pteridin-4-one
• CAS: 136778-66-0
• 化学式: C₉H₁₅N₅O
• 分子量: 209.251
• InChiKey: NABLTMGJMSJTNW-YFKPBYRVSA-N

物化性质

• 沸点：
  369.8±52.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  91.5
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-<(2(S)-aminopentyl)amino>-2,5-diamino-4(3H)-pyrimidinone 生成 6-propyl-7,8-dihydropterin 、 2-Amino-6-((S)-2-amino-pentylamino)-5-hydroxy-3H-pyrimidin-4-one 、 6(S)-propyl-5,6,7,8-tetrahydropterin
  参考文献：
  名称：

  Synthesis of tetrahydropteridine C6-stereoisomers, including N5-formyl-(6S)-tetrahydrofolic acid

  摘要：

  Chiral N1-protected vicinal diamines derived from amino acids were condensed with 2-amino-6-chloro-5-nitro-4(3H)-pyrimidinone, the nitro group reduced, and the amine deprotected. oxidative cyclization of the resulting triaminopyrimidinone via quinoid pyrimidine intermediates gave a quinoid dihydropteridine, which was then reduced to a tetrahydropteridine C6-stereoisomer. Thus, 6(R)- and 6(S)-propyltetrahydropterin were stereospecifically synthesized (99% enantiomeric purity) in good yield from D- and L-norvaline, respectively. Reductive alkylation of (p-aminobenzoyl)-L-glutamate with a nitropyrimidine aldehyde derived from D- or L-serine similarly afforded, after cyclization and reduction, (6R)- or (6S)-tetrahydrofolic acid. The latter was then converted to the natural isomer of leucovorin by regioselective N5-formylation with carbonyl diimidazole/formic acid without loss of enantiomeric purity.

  DOI：

  10.1021/jo00042a030

文献信息

• EP0631581A4
  申请人：——

  公开号：EP0631581A4

  公开（公告）日：1995-08-02
• INTERMEDIATES AND A PROCESS FOR SYNTHESIS OF TETRAHYDROPTERIDINE C6-STEREOISOMERS, INCLUDING (6S)-TETRAHYDROFOLATE AND N5-FORMYL-(6S)-TETRHYDROFOLATE
  申请人：BAILEY, StevenW.

  公开号：EP0631581A1

  公开（公告）日：1995-01-04
• US5198547A
  申请人：——

  公开号：US5198547A

  公开（公告）日：1993-03-30
• US5350851A
  申请人：——

  公开号：US5350851A

  公开（公告）日：1994-09-27
• [EN] INTERMEDIATES AND A PROCESS FOR SYNTHESIS OF TETRAHYDROPTERIDINE C6-STEREOISOMERS, INCLUDING (6S)-TETRAHYDROFOLATE AND N5-FORMYL-(6S)-TETRHYDROFOLATE
  申请人：BAILEY, Steven, W.

  公开号：WO1993019069A1

  公开（公告）日：1993-09-30

  (EN) Intermediates and a process for the synthesis of 6-monosubstituted tetrahydropteridine C6-stereoisomers, including (6S)-tetrahydrofolic acid. The intermediates are shown in their two enantiomeric forms as above, wherein R1 and R2 are the same or different and represent hydrogen, methyl, hydroxy, amino, alkyl or dialkylamino, alkoxy, benzyloxy, or benzylthio; R3 represents an alkene, alkyne, cycloalkyl, benzyl, alkyl (substituted with hydroxy, acetoxy, benzyloxy, alkoxy, alkylthio, amino, carboxy, oxo, or phosphate), a protected aldehyde, or (II) wherein n = 1 or 2, R4 is hydrogen, formyl, methyl, or propargyl, and ZZ represents an amino acid or amino acid polymer. Also, a process for tetrahydropteridine N5-formylation for the preparation of, for example, N5-formyl-(6S)-tetrahydrofolic acid.(FR) On décrit des intermédaires et un procédé relatifs à la synthèse de stéréo-isomères C6 de tétrahydroptéridine 6-monosubstituée. Ces intermédiaires sont reproduits sous leurs deux formes énantiomères comme ci-dessus: R1 et R2 sont identiques ou différentes et représentent hydrogène, méthyle, hydroxy, amino, alkyle ou dialkylamino, alcoxy, benzyloxy ou benzylthio; R3 représente un alcène, alcyne, cycloalkyle, benzyle, alkyle (substitué avec hydroxy, acétoxy, benzyloxy, alcoxy, alkylthio, amino, carboxy, oxo ou phosphate), un aldéhyde protégé, ou (II) où n = 1 ou 2, R4 représente hydrogène, formyle, méthyle ou propargyle, et ZZ représente un acide aminé ou un polymère d'acide aminé. On décrit aussi un procédé concernant la formylation N5 de la tétrahydroptéridine, ce qui permet de préparer par exemple l'acide N5-formyle-(6S)-tétrahydrofolique.