(2R,4S)-4-amino-4-phenylbutane-1,2-diol | 620989-96-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R,4S)-4-amino-4-phenylbutane-1,2-diol
• CAS: 620989-96-0
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: MWXNEPQRLUVWRY-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.43
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  66.48
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,5R)-5-[2-氟-6-(2-三甲基硅烷基乙氧基)嘌呤-9-基]-2-(羟基甲基)四氢呋喃-3-醇 、 (2R,4S)-4-amino-4-phenylbutane-1,2-diol 在 二甲基亚砜 、 N,N-二异丙基乙胺 、 溶剂黄146 、 sodium periodate 作用下， 以 水 为溶剂， 以42%的产率得到(6S,8R)-8-hydroxy-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-phenyl-5,6,7,8-tetrahydropyrimido[1,2-a]purin-10-one
  参考文献：
  名称：

  Stereoselective synthesis of the 1,N2-deoxyguanosine adducts of cinnamaldehyde. A stereocontrolled route to deoxyguanosine adducts of α,β-unsaturated aldehydes

  摘要：

  alpha,beta-Unsaturated aldehydes (enals) react with deoxyguanosine and have mutagenic potential. For higher enals, the reaction of deoxyguanosine gives diastereomeric 6-substituted 8-hydroxypyrimidopurinone products. These stereoisomers may have different local conformations in DNA, which may have biological consequences. We have developed a stereospecific synthesis of 1, N-2-deoxyguanosine adducts of cinnamaldehyde. The key step is the synthesis is a metal-promoted intramolecular C-H insertion reaction of nitrogen of an enantiomerically pure sulfamate ester. The approach may be general for the stereocontrolled synthesis of this class of DNA adducts and can be applied to the preparation of site-specifically adducted oligonucleotides. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.006
• 作为产物：
  描述：

  tert-butyl-[[(4S,6S)-2,2-dioxo-4-phenyloxathiazinan-6-yl]methoxy]-diphenylsilane 在 氢氧化钾 、 sodium t-butanolate 作用下， 以 甲醇 、 水 为溶剂， 生成 (2R,4S)-4-amino-4-phenylbutane-1,2-diol
  参考文献：
  名称：

  Stereoselective synthesis of the 1,N2-deoxyguanosine adducts of cinnamaldehyde. A stereocontrolled route to deoxyguanosine adducts of α,β-unsaturated aldehydes

  摘要：

  alpha,beta-Unsaturated aldehydes (enals) react with deoxyguanosine and have mutagenic potential. For higher enals, the reaction of deoxyguanosine gives diastereomeric 6-substituted 8-hydroxypyrimidopurinone products. These stereoisomers may have different local conformations in DNA, which may have biological consequences. We have developed a stereospecific synthesis of 1, N-2-deoxyguanosine adducts of cinnamaldehyde. The key step is the synthesis is a metal-promoted intramolecular C-H insertion reaction of nitrogen of an enantiomerically pure sulfamate ester. The approach may be general for the stereocontrolled synthesis of this class of DNA adducts and can be applied to the preparation of site-specifically adducted oligonucleotides. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.006