1,2:5,6-di-O-isopropylidene-3-O-(4-fluorophenoxy)thionocarbonyl-α-D-glucofuranose | 130534-83-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2:5,6-di-O-isopropylidene-3-O-(4-fluorophenoxy)thionocarbonyl-α-D-glucofuranose
• 英文别名: [(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxy-(4-fluorophenoxy)methanethione
• CAS: 130534-83-7
• 化学式: C₁₉H₂₃FO₇S
• 分子量: 414.452
• InChiKey: FKOCZXXTRFFPPK-IBEHDNSVSA-N

物化性质

• 沸点：
  457.3±55.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  96.7
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-(4-fluorophenoxy)thionocarbonyl-α-D-glucofuranose 在 三乙基硼 、 二苯基硅烷 、 氧气 作用下， 以 正己烷 、 苯 为溶剂， 反应 0.67h， 以94%的产率得到3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside
  参考文献：
  名称：

  自由基反应的发明。第XXXI部分。二苯硅烷：一种通过醇的硫代羰基衍生物对醇进行脱氧，通过异腈进行脱氨基，以及通过自由基链化学对溴和碘化合物进行脱卤的试剂

  摘要：

  各种thionocarbonates和醇的黄原酸盐和二的-xanthates VIC -diols容易脱氧成相应的烃或烯烃，而溴化物和碘化物与以良好的收率diphenylphenylsilane脱卤。

  DOI：

  10.1016/s0040-4020(01)87198-2
• 作为产物：
  描述：

  4-氟苯基氯硫代甲酸酯 、 双丙酮葡萄糖 在 吡啶 、 N-羟基丁二酰亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以76%的产率得到1,2:5,6-di-O-isopropylidene-3-O-(4-fluorophenoxy)thionocarbonyl-α-D-glucofuranose
  参考文献：
  名称：

  The invention of radical reactions. Part XXIX. Radical mono- and dideoxygenations with silanes

  摘要：

  Thionocarbonates and xanthates of primary and secondary alcohols, as well as bis-xanthates of vic-diols are readily deoxygenated to the corresponding hydrocarbons or olefins with phenylsilane, triphenylsilane, and triethylsilane in good yield.

  DOI：

  10.1016/s0040-4020(01)80380-x

文献信息

• Hypophosphorous acid and its salts: New reagents for radical chain deoxygenation, dehalogenation and deamination
  作者：Derek H.R. Barton、Doo Ok Jang、Joseph Cs. Jaszberenyi

  DOI：10.1016/0040-4039(92)89012-2

  日期：1992.9

  Thionocarbonates and xanthates of alcohols, bromides, iodides and isonitriles can be transfromed to the corresponding hydrocarbons with hypophosphorous acid or its salts in radical chain reactions.

  醇，溴化物，碘化物和异腈的亚硫代碳酸盐和黄原酸酯可以在次要链反应中与次磷酸或其盐转变为相应的烃。
• Radical mono- and dideoxygenations with the triethylsilane + benzoyl peroxide system.
  作者：Derek H.R. Barton、Doo Ok Jang、Joseph Cs. Jaszberenyi

  DOI：10.1016/0040-4039(91)80472-i

  日期：1991.12

  Thionocarbonates and xanthates of primary and secondary alcohols, as well as dixanthates of vic-diols can easily be deoxygenated to the corresponding hydrocarbons or olefins with triethylsilane and benzoyl peroxide in high-yielding radical reactions.
• Radical deoxygenations and dehalogenations with dialkyl phosphites as hydrogen atom sources
  作者：Derek H.R. Barton、Doo Ok Jang、Joseph Cs. Jaszberenyi

  DOI：10.1016/s0040-4039(00)74198-0

  日期：1992.4

  Thionocarbonates and xanthates of alcohols, and various halides and phenylselenides can be transformed to the corresponding hydrocarbons with alkyl phosphites and benzoyl peroxide in most cases in high-yielding radical reactions.
• The invention of radical reactions. Part 32. Radical deoxygenations, dehalogenations, and deaminations with dialkyl phosphites and hypophosphorous acid as hydrogen sources
  作者：Derek H. R. Barton、Doo Ok Jang、Joseph C. Jaszberenyi

  DOI：10.1021/jo00076a054

  日期：1993.11

  Reagents, containing a P-H bond, such as dimethyl phosphite, diethyl phosphite, hypophosphorous acid and various salts of hypophosphorous acid are effective radical reducing agents for organic halides, thionoesters, and isocyanides affording high yields of the corresponding hydrocarbons. Reduction of tertiary phenyl selenides and tertiary nitro compounds are not efficient under these conditions. Olefination of 1,2-diols is also accomplished via the corresponding thiocarbonyl derivatives using hypophosphorous acid and triethylamine in the presence of a suitable ''sacrificial olefin'' in moderate to good yields.
• An improved radical chain procedure for the deoxygenation of secondary and primary alcohols using diphenylsilane as hydrogen atom donor and triethylborane-air as initiator
  作者：Derek H.R. Barton、Ok Jang Doo、Joseph Cs. Jaszberenyi

  DOI：10.1016/s0040-4039(00)97705-0

  日期：1990.1