(2R,4R)-4-amino-4-phenylbutane-1,2-diol | 143216-63-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R,4R)-4-amino-4-phenylbutane-1,2-diol
• CAS: 143216-63-1
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: MWXNEPQRLUVWRY-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,4R)-4-amino-4-phenylbutane-1,2-diol 、 (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 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(6R,8S)-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：

  苄基三苯基氯化膦 在 palladium on activated charcoal 吡啶 、 咪唑 、 dirhodium tetraacetate 、 氢氧化钾 、 正丁基锂 、 甲酸 、 氯磺酰异氰酸酯 、 碘苯二乙酸 、 氢气 、 magnesium oxide 、 对甲苯磺酸 、 sodium t-butanolate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 (2R,4R)-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

文献信息

• Ring opening of the epoxide moiety of (2S, 3S, 4S)-4-amino-2,3-epoxy-1-alkanol and its derivatives: A key role of Ti(O-i-Pr)4 as a mild catalyst
  作者：Hirokazu Urabe、Yoshiaki Aoyama、Fumie Sato

  DOI：10.1016/0040-4020(92)80014-7

  日期：1992.7

  (2S, 3S, 4S)-4-Amino-2,3-epoxy-1-alkanol gave 4-amino-1,3-alkanediol or 3,4-imino-1,2-alkanediol with Dibal or Ti(O-i-Pr)4 respectively and, after introduction of Boc group to its amino group, afforded a 4-amino-1,2,3-alkanetriol derivative under the influence of Ti(O-i-Pr)4.

  （2 S，3 S，4 S）-4-氨基-2,3-环氧-1-链烷醇与丁二醛或Ti生成4-氨基-1,3-链烷二醇或3,4-亚氨基-1,2-链烷二醇（O- i- Pr）4，并且在将Boc基团引入其氨基后，在Ti（O- i- Pr）4的影响下得到4-氨基-1,2,3-链烷三醇衍生物。
• Chiral .alpha.,.beta.-epoxy group as a stereocontrolling element in the reduction of N-metalloimines. A short synthesis of anti-epoxy amines
  作者：Hirokazu Urabe、Yoshiaki Aoyama、Fumie Sato

  DOI：10.1021/jo00045a006

  日期：1992.9

  Reduction of the alpha,beta-epoxy N-metalloimines generated from the TBS ether of (2S,3S)-3-cyano-2,3-epoxy-1-propanol (1), Grignard reagents, and Me3SiCl with NaBH4 afforded the TBS ethers of (2S,3S,4S)-4-amino-2,3-epoxy-1-alkanols 4 with diastereoselectivities of up to 95:5.
• Stereoselective synthesis of the 1,N2-deoxyguanosine adducts of cinnamaldehyde. A stereocontrolled route to deoxyguanosine adducts of α,β-unsaturated aldehydes
  作者：Mansoureh Rezaei、Thomas M. Harris、Carmelo J. Rizzo

  DOI：10.1016/j.tetlet.2003.08.006

  日期：2003.9

  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.