[(2S)-1-[tert-butyl(diphenyl)silyl]oxy-4-phenylbutan-2-yl] sulfamate | 620990-00-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: [(2S)-1-[tert-butyl(diphenyl)silyl]oxy-4-phenylbutan-2-yl] sulfamate
• CAS: 620990-00-3
• 化学式: C₂₆H₃₃NO₄SSi
• 分子量: 483.704
• InChiKey: MWBILKQWOJQHLH-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  87
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2S)-1-[tert-butyl(diphenyl)silyl]oxy-4-phenylbutan-2-yl] sulfamate 在 dirhodium tetraacetate 、 碘苯二乙酸 、 magnesium oxide 、 sodium t-butanolate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 [(2R,4R)-1-[tert-butyl(diphenyl)silyl]oxy-4-phenyl-4-(phenylmethoxycarbonylamino)butan-2-yl] acetate
  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 、 正丁基锂 、 甲酸 、 氯磺酰异氰酸酯 、 氢气 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 [(2S)-1-[tert-butyl(diphenyl)silyl]oxy-4-phenylbutan-2-yl] sulfamate
  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

• 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.