(6R,8S)-2,2,6,9,12,12-hexamethyl-10-oxo-3,3-diphenyl-4,11-dioxa-9-aza-3-silatridecane-8-carboxylic acid | 1027190-57-3

• 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: (6R,8S)-2,2,6,9,12,12-hexamethyl-10-oxo-3,3-diphenyl-4,11-dioxa-9-aza-3-silatridecane-8-carboxylic acid
• 英文别名: (2S,4R)-5-[tert-butyl(diphenyl)silyl]oxy-4-methyl-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pentanoic acid
• CAS: 1027190-57-3
• 化学式: C₂₈H₄₁NO₅Si
• 分子量: 499.723
• InChiKey: SYRXOOQDHVTWMV-QPPBQGQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6R,8S)-2,2,6,9,12,12-hexamethyl-10-oxo-3,3-diphenyl-4,11-dioxa-9-aza-3-silatridecane-8-carboxylic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 26.33h， 生成 (6R,8S,11R,14S)-methyl 8-(tert-butoxycarbonyl(methyl)amino)-14-((R)-methoxy(phenyl)methyl)-2,2,6,11-tetramethyl-9,12-dioxo-3,3-diphenyl-4-oxa-10,13-diaza-3-silapentadecan-15-oate
  参考文献：
  名称：

  Synthesis of the ‘southern’ tripeptide of Cyclomarins A and C having novel anti-tuberculocidal mode of action

  摘要：

  The synthesis of the 'southern' tripeptide of Cyclomarins A and C has been described which includes two unusual amino acids. The unusual amino acids have been synthesized and coupled with L-alanine to obtain the tripeptide. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.026
• 作为产物：
  描述：

  tert-butyl [(1S,3R)-4-hydroxy-1-(hydroxymethyl)-3-methylbutyl]carbamate 在 咪唑 、 甲醇 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 55.5h， 生成 (6R,8S)-2,2,6,9,12,12-hexamethyl-10-oxo-3,3-diphenyl-4,11-dioxa-9-aza-3-silatridecane-8-carboxylic acid
  参考文献：
  名称：

  Synthesis of the ‘southern’ tripeptide of Cyclomarins A and C having novel anti-tuberculocidal mode of action

  摘要：

  The synthesis of the 'southern' tripeptide of Cyclomarins A and C has been described which includes two unusual amino acids. The unusual amino acids have been synthesized and coupled with L-alanine to obtain the tripeptide. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.026

文献信息

• Syntheses of four unusual amino acids, constituents of cyclomarin A
  作者：Hideyuki Sugiyama、Takayuki Shioiri、Fumiaki Yokokawa

  DOI：10.1016/s0040-4039(02)00607-x

  日期：2002.5

  amino acids, constituents of cyclomarin A, are described. The protected N-methylhydroxyleucine 2 was synthesized using Evans’ asymmetric azide-transfer reaction. The unusual amino acid 3 was prepared via diastereoselective methylation of the l-aspartic acid derived lactone 13. The stereoselective formation of threo-β-methoxyphenylalanine 4 was performed via aldol reaction using Schöllkopf's chiral glycine

  描述了四种非常规氨基酸的立体选择性合成，它们是环marinA的组成部分。使用Evans的不对称叠氮化物转移反应合成了被保护的N-甲基羟基亮氨酸2。通过L-天冬氨酸衍生的内酯13的非对映选择性甲基化制备了不寻常的氨基酸3。使用Schöllkopf's手性甘氨酸烯醇酸酯通过醛醇缩合反应进行苏-β-甲氧基苯基丙氨酸4的立体选择性形成。通过AQN配体促进的Sharpless区域逆向不对称氨基羟基化方案实现了N-反向的戊烯基色氨酸5的合成。
• Synthesis of the ‘southern’ tripeptide of Cyclomarins A and C having novel anti-tuberculocidal mode of action
  作者：Kurapati Sathish、Gangireddy Pavan Kumar Reddy、Prathama S. Mainkar、Srivari Chandrasekhar

  DOI：10.1016/j.tetasy.2011.08.026

  日期：2011.7

  The synthesis of the 'southern' tripeptide of Cyclomarins A and C has been described which includes two unusual amino acids. The unusual amino acids have been synthesized and coupled with L-alanine to obtain the tripeptide. (C) 2011 Elsevier Ltd. All rights reserved.