ethyl 6-[(3aR,4R,6S,6aS)-4-[6-(dibenzoylamino)purin-9-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-5,6-dibromo-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate | 916595-33-0

• 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: ethyl 6-[(3aR,4R,6S,6aS)-4-[6-(dibenzoylamino)purin-9-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-5,6-dibromo-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 916595-33-0
• 化学式: C₃₉H₄₄Br₂N₆O₉
• 分子量: 900.621
• InChiKey: NHMFIDVITUMARJ-RMXZYJSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  56
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  173
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  ethyl 6-[(3aR,4R,6S,6aS)-4-[6-(dibenzoylamino)purin-9-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-5,6-dibromo-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate 以20 mg的产率得到2-amino-5-bromo-5(E)-[5'-deoxyadenosin-5'-ylidene]pentanoic acid
  参考文献：
  名称：

  S-Adenosylhomocysteine Analogues with the Carbon-5‘ and Sulfur Atoms Replaced by a Vinyl Unit

  摘要：

  Cross-metathesis of suitably protected 5'-deoxy-5'-methyleneadenosines with racemic and chiral N-Boc-protected six-carbon amino acids bearing a terminal double bond in the presence of the Hoveyda-Grubbs catalyst gave adenosylhomocysteine analogues with the C5'-C6' double bond. Bromination with pyridinium tribromide and dehydrobromination with DBU followed by standard deprotections yielded the 5'-(bromo) vinyl analogue.

  DOI：

  10.1021/ol062026m
• 作为产物：
  描述：

  ethyl 2-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate 在 pyridinium hydrobromide perbromide 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 生成 ethyl 6-[(3aR,4R,6S,6aS)-4-[6-(dibenzoylamino)purin-9-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-5,6-dibromo-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
  参考文献：
  名称：

  S-Adenosylhomocysteine Analogues with the Carbon-5‘ and Sulfur Atoms Replaced by a Vinyl Unit

  摘要：

  Cross-metathesis of suitably protected 5'-deoxy-5'-methyleneadenosines with racemic and chiral N-Boc-protected six-carbon amino acids bearing a terminal double bond in the presence of the Hoveyda-Grubbs catalyst gave adenosylhomocysteine analogues with the C5'-C6' double bond. Bromination with pyridinium tribromide and dehydrobromination with DBU followed by standard deprotections yielded the 5'-(bromo) vinyl analogue.

  DOI：

  10.1021/ol062026m

文献信息

• <i>S-</i>Adenosylhomocysteine Analogues with the Carbon-5‘ and Sulfur Atoms Replaced by a Vinyl Unit
  作者：Daniela Andrei、Stanislaw F. Wnuk

  DOI：10.1021/ol062026m

  日期：2006.10.1

  Cross-metathesis of suitably protected 5'-deoxy-5'-methyleneadenosines with racemic and chiral N-Boc-protected six-carbon amino acids bearing a terminal double bond in the presence of the Hoveyda-Grubbs catalyst gave adenosylhomocysteine analogues with the C5'-C6' double bond. Bromination with pyridinium tribromide and dehydrobromination with DBU followed by standard deprotections yielded the 5'-(bromo) vinyl analogue.