tert-butyl (2R,3S)-3-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]-3-hydroxy-2-[3-[[(2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]propylamino]propanoate | 1239956-23-0

• 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: tert-butyl (2R,3S)-3-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]-3-hydroxy-2-[3-[[(2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]propylamino]propanoate
• CAS: 1239956-23-0
• 化学式: C₄₄H₇₅N₅O₁₁Si₂
• 分子量: 906.277
• InChiKey: XFKABVZOZNGGAC-DQSIVDKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  62.0
• 可旋转键数：
  19.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  208.54
• 氢给体数：
  5.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  benzyl N-[(2S)-1-(3-aminopropylamino)-4-methyl-1-oxopentan-2-yl]carbamate;hydrochloride 、 在 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 以52%的产率得到tert-butyl (2R,3S)-3-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]-3-hydroxy-2-[3-[[(2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]propylamino]propanoate
  参考文献：
  名称：

  Efficient synthesis of the core structure of muraymycin and caprazamycin nucleoside antibiotics based on a stereochemically revised sulfur ylide reaction

  摘要：

  The reaction of protected uridine 5'-aldehydes with sulfur ylides has been reinvestigated Further transformation of the resulting epoxide product provided a compound of which a single crystal for X-ray diffraction was obtained. As a consequence from the elucidated structure, the stereochemical configuration of the epoxide furnished by the sulfur ylide reaction was revised. Based on these results, an efficient synthesis of the core structure of the naturally occurring muraymycin and caprazamycin nucleoside antibiotics was developed. (C) 2010 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tetasy.2010.03.037

文献信息

• Efficient synthesis of the core structure of muraymycin and caprazamycin nucleoside antibiotics based on a stereochemically revised sulfur ylide reaction
  作者：Anatol P. Spork、Stefan Koppermann、Birger Dittrich、Regine Herbst-Irmer、Christian Ducho

  DOI：10.1016/j.tetasy.2010.03.037

  日期：2010.4

  The reaction of protected uridine 5'-aldehydes with sulfur ylides has been reinvestigated Further transformation of the resulting epoxide product provided a compound of which a single crystal for X-ray diffraction was obtained. As a consequence from the elucidated structure, the stereochemical configuration of the epoxide furnished by the sulfur ylide reaction was revised. Based on these results, an efficient synthesis of the core structure of the naturally occurring muraymycin and caprazamycin nucleoside antibiotics was developed. (C) 2010 Elsevier Ltd. All rights reserved