1-[2,5-bis(O-tert-butyldimethylsilyl)-3-C-methoxycarbonylmethyl-β-D-xylofuranosyl]uracil | 272780-86-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-[2,5-bis(O-tert-butyldimethylsilyl)-3-C-methoxycarbonylmethyl-β-D-xylofuranosyl]uracil
• 英文别名: 2',5'-di-O-tert-butyldimethylsilyl-3'-C-(methoxycarbonylmethyl)xylouridine；methyl 2-[(2R,3S,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-3-yl]acetate
• CAS: 272780-86-6
• 化学式: C₂₄H₄₄N₂O₈Si₂
• 分子量: 544.793
• InChiKey: IIDBYYRBAGXSHW-QHCFZIRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-[2,5-bis(O-tert-butyldimethylsilyl)-3-C-methoxycarbonylmethyl-β-D-xylofuranosyl]uracil 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 14.0h， 以46%的产率得到2',5'-di-O-tert-butyldimethylsilyl-3'-C-(2-hydroxyethyl)xylouridine
  参考文献：
  名称：

  具有非经典δ/ɛ/ζ扭转角组合的木糖构螺旋螺iro，ζ-D-CNA的合成

  摘要：

  从尿嘧啶核苷中描述了螺旋木糖基的非对映异构体的合成，其中ζ和ζ扭转角由二氧杂磷环烷环结构（D-CNA家族）立体控制。 Mukaïyama的醛醇缩合反应是关键反应。的NMR结构分析结果表明，δ，ɛ和ζ扭转（的角度小号C3' ，- [R P） -和（小号C3' ，小号P）构型的木糖-ɛ，ζ-d-CNA TT二聚体被限制在{δ，ɛ，ζ} = {顺，反，gauche } +或{顺，反，gauche（-）}构象分别与A型或B型双链体中通常观察到的构象显着不同。

  DOI：

  10.1016/j.tet.2007.08.098
• 作为产物：
  描述：

  (3''-R)-1-[2',5'-bis(O-tert-butyldimethylsilyl)-3'-deoxy-β-D-xylofuranosyl]uracil-3'-spiro-2''-(3''-methoxycarbonyloxirane) 在 一水合肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 为溶剂， 反应 722.0h， 生成 1-[2,5-bis(O-tert-butyldimethylsilyl)-3-C-methoxycarbonylmethyl-β-D-xylofuranosyl]uracil
  参考文献：
  名称：

  Highly Stereoselective Synthesis and Biological Properties of Nucleoside Analogues Bearing a Spiro Inserted Oxirane Ring

  摘要：

  Starting from 2',5'-di-O-TBDMS-3'-ketouridine 1 or its thymine analogue 2, both xylo (3-10) and ribo (20) epimers of a series of 3"-substituted 3'-spironucleosides have been obtained in good yields and with a total stereoselectivity. Most new compounds were moderately cytotoxic with in some cases slightly selective antiproliferative activities. None of these compounds was active against HIV, but some other antiviral activities against HSV-2, CMV, EBV, or VZV, in the micromolar range, were noted in specific cases.

  DOI：

  10.1080/15257770008035024

文献信息

• Synthesis of spiro ɛ,ζ-D-CNA in xylo configuration featuring noncanonical δ/ɛ/ζ torsion angle combination
  作者：Christelle Dupouy、Pierre Lavedan、Jean-Marc Escudier

  DOI：10.1016/j.tet.2007.08.098

  日期：2007.11

  The synthesis of diastereoisomers of spiro xylo-ɛ,ζ-D-CNA dinucleotide building units of nucleic acids, in which the ɛ and ζ torsional angles are stereocontrolled by a dioxaphosphorinane ring structure (D-CNA family), is described from uridine with a Mukaïyama's aldol condensation as key reaction. The NMR structure analysis showed that δ, ɛ and ζ torsional angles of the (SC3′,RP)- and (SC3′,SP)-configured

  从尿嘧啶核苷中描述了螺旋木糖基的非对映异构体的合成，其中ζ和ζ扭转角由二氧杂磷环烷环结构（D-CNA家族）立体控制。 Mukaïyama的醛醇缩合反应是关键反应。的NMR结构分析结果表明，δ，ɛ和ζ扭转（的角度小号C3' ，- [R P） -和（小号C3' ，小号P）构型的木糖-ɛ，ζ-d-CNA TT二聚体被限制在δ，ɛ，ζ} = 顺，反，gauche } +或顺，反，gauche（-）}构象分别与A型或B型双链体中通常观察到的构象显着不同。
• Highly Stereoselective Synthesis and Biological Properties of Nucleoside Analogues Bearing a Spiro Inserted Oxirane Ring
  作者：Jean M. J. Tronchet、Imre Kovacs、Michel Seman、Pierre Dilda、Erik De Clercq、Jan Balzarini

  DOI：10.1080/15257770008035024

  日期：2000.4

  Starting from 2',5'-di-O-TBDMS-3'-ketouridine 1 or its thymine analogue 2, both xylo (3-10) and ribo (20) epimers of a series of 3"-substituted 3'-spironucleosides have been obtained in good yields and with a total stereoselectivity. Most new compounds were moderately cytotoxic with in some cases slightly selective antiproliferative activities. None of these compounds was active against HIV, but some other antiviral activities against HSV-2, CMV, EBV, or VZV, in the micromolar range, were noted in specific cases.