1-(2-O-{[1-(5-(({6-N-[1-(4,4'-dimethoxytrityl)-D-biotinoyl]aminohexanoyl}amino)methyl)-2-nitrophenyl)ethoxy]methyl}-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl)uracil | 1241387-99-4

• 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: 1-(2-O-{[1-(5-(({6-N-[1-(4,4'-dimethoxytrityl)-D-biotinoyl]aminohexanoyl}amino)methyl)-2-nitrophenyl)ethoxy]methyl}-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl)uracil
• 英文别名: 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]-N-[[3-[1-[[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl]oxymethoxy]ethyl]-4-nitrophenyl]methyl]hexanamide
• CAS: 1241387-99-4
• 化学式: C₇₇H₈₅N₇O₁₆S
• 分子量: 1396.63
• InChiKey: PWSULWOIAQXTFI-VXQKCVOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  101
• 可旋转键数：
  33
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  305
• 氢给体数：
  5
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  1-(2-O-{[1-(5-(({6-N-[1-(4,4'-dimethoxytrityl)-D-biotinoyl]aminohexanoyl}amino)methyl)-2-nitrophenyl)ethoxy]methyl}-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl)uracil 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以47%的产率得到1-[3-O-cyanoethoxy(diisopropylamino)phosphino-2-O-{[1-(5-(({6-N-[1-(4,4'-dimethoxytrityl)-D-biotinoyl]aminohexanoyl}amino)methyl)-2-nitrophenyl)ethoxy]methyl}-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]uracil
  参考文献：
  名称：

  Convenient RNA Synthesis Using a Phosphoramidite Possessing a Biotinylated Photocleavable Group

  摘要：

  A convenient RNA synthesis using a biotin streptavidin interaction and a photocleavable protecting group is described. The biotinylated photocleavable group was introduced at the 2'-position of the uridine derivative. Using the phosphoramidite 12, we attempted the synthesis of a 21mer RNA, which is pure enough to show potent RNAi activity compared with a conventionally prepared and HPLC-purified 21mer RNA with the same sequence.

  DOI：

  10.1021/ol101489v
• 作为产物：
  描述：

  6-(1-N-(4,4'-dimethoxytrityl)-D-(+)-biotinoyl)aminohexanoic acid 、 1-(2-O-{[1-(5-(aminomethyl)-2-nitrophenyl)ethoxy]methyl}-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl)uracil 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以89%的产率得到1-(2-O-{[1-(5-(({6-N-[1-(4,4'-dimethoxytrityl)-D-biotinoyl]aminohexanoyl}amino)methyl)-2-nitrophenyl)ethoxy]methyl}-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl)uracil
  参考文献：
  名称：

  Convenient RNA Synthesis Using a Phosphoramidite Possessing a Biotinylated Photocleavable Group

  摘要：

  A convenient RNA synthesis using a biotin streptavidin interaction and a photocleavable protecting group is described. The biotinylated photocleavable group was introduced at the 2'-position of the uridine derivative. Using the phosphoramidite 12, we attempted the synthesis of a 21mer RNA, which is pure enough to show potent RNAi activity compared with a conventionally prepared and HPLC-purified 21mer RNA with the same sequence.

  DOI：

  10.1021/ol101489v

文献信息

• Convenient RNA Synthesis Using a Phosphoramidite Possessing a Biotinylated Photocleavable Group
  作者：Kota Tomaya、Mayumi Takahashi、Noriaki Minakawa、Akira Matsuda

  DOI：10.1021/ol101489v

  日期：2010.9.3

  A convenient RNA synthesis using a biotin streptavidin interaction and a photocleavable protecting group is described. The biotinylated photocleavable group was introduced at the 2'-position of the uridine derivative. Using the phosphoramidite 12, we attempted the synthesis of a 21mer RNA, which is pure enough to show potent RNAi activity compared with a conventionally prepared and HPLC-purified 21mer RNA with the same sequence.