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α-1-chloro-2-deoxy-2-fluoro-3,5-di-O-(triisopropylsilyl)-D-arabinofuranose | 1173700-31-6

中文名称
——
中文别名
——
英文名称
α-1-chloro-2-deoxy-2-fluoro-3,5-di-O-(triisopropylsilyl)-D-arabinofuranose
英文别名
1-deoxy-1-chloro-2-deoxy-2-fluoro-3,5-di-O-(triisopropylsilyl)-D-arabino-1,4-furanose;[(2R,3R,4S,5R)-5-chloro-4-fluoro-2-[tri(propan-2-yl)silyloxymethyl]oxolan-3-yl]oxy-tri(propan-2-yl)silane
α-1-chloro-2-deoxy-2-fluoro-3,5-di-O-(triisopropylsilyl)-D-arabinofuranose化学式
CAS
1173700-31-6
化学式
C23H48ClFO3Si2
mdl
——
分子量
483.255
InChiKey
KFTRJMIUBBDXHR-ACESQOTJSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    441.1±45.0 °C(Predicted)
  • 密度:
    0.96±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    8.04
  • 重原子数:
    30
  • 可旋转键数:
    11
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    1.0
  • 拓扑面积:
    27.7
  • 氢给体数:
    0
  • 氢受体数:
    4

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

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文献信息

  • Efficient Syntheses of Clofarabine and Gemcitabine From 2-Deoxyribonolactone
    作者:Yana Cen、Anthony A. Sauve
    DOI:10.1080/15257771003597758
    日期:2010.2.26
    The development of a new methodology to achieve electrophilic fluorination of triisopropylsilyl-protected 2-deoxyribonolactone has been employed to synthesize clofarabine and gemcitabine with improved synthetic efficiency versus prior synthetic methods. These studies highlight the versatility of this new methodology to obtain medically relevant 2'-fluoronucleosides.
  • Diastereocontrolled Electrophilic Fluorinations of 2-Deoxyribonolactone: Syntheses of All Corresponding 2-Deoxy-2-fluorolactones and 2′-Deoxy-2′-fluoro-NAD<sup>+</sup>s
    作者:Yana Cen、Anthony A. Sauve
    DOI:10.1021/jo900637f
    日期:2009.8.21
    Methods to construct 2'-deoxy-2'-fluoro nucleosides have undergone limited improvement in the last 20 years in spite of the substantially increased value of these compounds as pharmaceuticals and as tools for studying biological processes. We herein describe a consolidated approach to synthesize precursors to these commercially and scientifically valuable compounds via diastereocontrolled fluorination of the readily available precursor 2-deoxy-D-ribonolactone. With employment of appropriate sterically bulky silyl protecting groups at the 3 and 5 positions, controlled electrophilic fluorination of the Li-ribonolactone enolate by N-fluorodibenzenesulfonamide yielded the corresponding 2-deoxy-2-fluoroarabinolactone in high isolated yield (72%) The protected 2-deoxy-2,2-difluororibonolactone was obtained similarly in high yield from a second round of electrophilic fluorination (two steps, 51% from protected ribonolactone starting material). Accomplishment of the difficult ribofluorination of the lactone was achieved by the directive effects of a diastereoselectively installed (x-trimethylsilyl group. Electrophilic fluorination of a protected 2-deoxy-2-trimethylsilylarabinolactone via enolate generation provided the protected 2-deoxy-2-fluororibolactone as the exclusive fluorinated product. The reaction also yielded the starting material, the desilylated protected 2-deoxyribonolactone, which was recycled to provide a 38% chemical yield of the fluorinated product (versus initial protected ribonolactone),after consecutive silylation and fluorination cycles. Using our fluorinated sugar precursors, we prepared the 2'-fluoroarabino-, 2'-fluororibo-, and 2',2'-difluoronicotinamide adenine dinucleotides (NAD(+)) of potential biological interest. These syntheses provide the most consolidated and efficient methods for production of sugar precursors of 2'-deoxy-2'-fluoronucleosides and have the advantage of utilizing an air-stable electrophilic fluorinating agent. The fluorinated NAD(+)s are anticipated to be useful for studying a variety of cellular metabolic and signaling processes.
  • [EN] HALOGENATED 2-DEOXY-LACTONES, 2'-DEOXY--NUCLEOSIDES, AND DERIVATIVES THEREOF<br/>[FR] 2-DÉSOXY-LACTONES HALOGÉNÉES, 2'-DÉSOXY-NUCLÉOSIDES, ET LEURS DÉRIVÉS
    申请人:UNIV CORNELL
    公开号:WO2011003018A9
    公开(公告)日:2012-11-08
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同类化合物

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