methyl 6-(1-N-(4,4'-dimethoxytrityl)-D-(+)-biotinoyl)aminohexanoate | 874889-84-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: methyl 6-(1-N-(4,4'-dimethoxytrityl)-D-(+)-biotinoyl)aminohexanoate
• 英文别名: methyl 6-[5-[(3aR,6S,6aS)-3-[bis(4-methoxyphenyl)-phenylmethyl]-2-oxo-3a,4,6,6a-tetrahydro-1H-thieno[3,4-d]imidazol-6-yl]pentanoylamino]hexanoate
• CAS: 874889-84-6
• 化学式: C₃₈H₄₇N₃O₆S
• 分子量: 673.874
• InChiKey: MARKLOGCBSAZKY-UEMWQVMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  48
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 6-(1-N-(4,4'-dimethoxytrityl)-D-(+)-biotinoyl)aminohexanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 22.0h， 以90%的产率得到6-(1-N-(4,4'-dimethoxytrityl)-D-(+)-biotinoyl)aminohexanoic acid
  参考文献：
  名称：

  Synthesis of the Ribosomal P-Site Substrate CCA-pcb

  摘要：

  CCA-pcb (cytidylyl-(3'5')-cytidylyl-(3'5')-3'(2')-O-(N-(6-D-(+)-biotinoylaminohexanoyl)-L-phenylalanyl)adenosine), a ribosomal P-site substrate, was synthesized by phosphoramidite chemistry in 26 steps with an overall yield of 18%, starting from biotin. The synthesis relies on the judicious selection of orthogonal silyl protecting groups for the 5'-hydroxyls and acid-labile protecting groups (DMTr, AcE, and MeE) at other reactive sites to ensure the intactness of the labile ester. Both X-esterification and nucleotide coupling were accomplished by in situ activation with imidazolium ions.

  DOI：

  10.1021/ol052484f
• 作为产物：
  描述：

  D-生物素甲酯 在 吡啶 、 sodium hydroxide 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 为溶剂， 反应 17.0h， 生成 methyl 6-(1-N-(4,4'-dimethoxytrityl)-D-(+)-biotinoyl)aminohexanoate
  参考文献：
  名称：

  Synthesis of the Ribosomal P-Site Substrate CCA-pcb

  摘要：

  CCA-pcb (cytidylyl-(3'5')-cytidylyl-(3'5')-3'(2')-O-(N-(6-D-(+)-biotinoylaminohexanoyl)-L-phenylalanyl)adenosine), a ribosomal P-site substrate, was synthesized by phosphoramidite chemistry in 26 steps with an overall yield of 18%, starting from biotin. The synthesis relies on the judicious selection of orthogonal silyl protecting groups for the 5'-hydroxyls and acid-labile protecting groups (DMTr, AcE, and MeE) at other reactive sites to ensure the intactness of the labile ester. Both X-esterification and nucleotide coupling were accomplished by in situ activation with imidazolium ions.

  DOI：

  10.1021/ol052484f