α-D-1,2:5,6-di-O-isopropylidene-3-O-[(methylthio)thiocarbonyl]-glucofuranose | 143037-49-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-1,2:5,6-di-O-isopropylidene-3-O-[(methylthio)thiocarbonyl]-glucofuranose
• 英文别名: 1,2:5,6-di-O-isopropylidene-3-O-(methylthio)thiocarbonyl-α-D-glucofuranose；O-[(3aR,5R,6S,6aR)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] methylsulfanylmethanethioate
• CAS: 143037-49-4
• 化学式: C₁₄H₂₂O₆S₂
• 分子量: 350.457
• InChiKey: ABYFQWZWTAVGKO-OGBGREFGSA-N

物化性质

• 沸点：
  427.2±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  α-D-1,2:5,6-di-O-isopropylidene-3-O-[(methylthio)thiocarbonyl]-glucofuranose 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium sulfide 、 sodium tetrahydroborate 、 sodium periodate 、 偶氮二异丁腈 、 Dowex 50W-XB(H) 、 水 、 三正丁基氢锡 、 四丁基碘化铵 、 三乙酰氧基硼氢化钠 、 sodium hydride 、 potassium carbonate 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (3'R,5'R)-1-<5'-<(benzyloxy)methyl>tetrahydro-3'-thienyl>-9H-purin-6-amine
  参考文献：
  名称：

  四氢噻吩核苷可作为潜在的抗HIV药物

  摘要：

  已经从D-葡萄糖以同手性形式制备了一系列新的四氢噻吩核苷，并在全细胞测定中被评估为抗HIV药物。

  DOI：

  10.1016/0040-4039(91)80867-6
• 作为产物：
  描述：

  甲醇 、 二硫化碳 、 1,2:5,6-diacetone-D-glucose 在 咪唑 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以80%的产率得到α-D-1,2:5,6-di-O-isopropylidene-3-O-[(methylthio)thiocarbonyl]-glucofuranose
  参考文献：
  名称：

  3-Deoxy-β-D-ribo-hexopyranose (3-deoxy-β-D-glucopyranose)

  摘要：

  The beta- pyranose form, ( III), of 3- deoxy- D- ribo- hexose ( 3- deoxy- D- glucose), C6H12O5, crystallizes from water at 298 K in a slightly distorted C-4(1) chair conformation. Structural analyses of ( III), beta- D- glucopyranose, ( IV), and 2- deoxy- beta- D-arabinohexopyranose ( 2- deoxy- beta- D- glucopyranose), ( V), show significantly different C - O bond torsions involving the anomeric carbon, with the H - C - O - H torsion angle approaching an eclipsed conformation in ( III) (. 10.9 degrees) compared with 32.8 and 32.5 degrees in ( IV) and ( V), respectively. Ring carbon deoxygenation significantly affects the endo- and exocyclic C - C and C - O bond lengths throughout the pyranose ring, with longer bonds generally observed in the monodeoxygenated species ( III) and ( V) compared with ( IV). These structural changes are attributed to differences in exocyclic C - O bond conformations and/ or hydrogenbonding patterns superimposed on the direct ( intrinsic) effect of monodeoxygenation. The exocyclic hydroxymethyl conformation in ( III) ( gt) differs from that observed in ( IV) and ( V) ( gg).

  DOI：

  10.1107/s0108270107038553

文献信息

• Complexes of Borane and N-Heterocyclic Carbenes: A New Class of Radical Hydrogen Atom Donor
  作者：Shau-Hua Ueng、Malika Makhlouf Brahmi、Étienne Derat、Louis Fensterbank、Emmanuel Lacôte、Max Malacria、Dennis P. Curran

  DOI：10.1021/ja804150k

  日期：2008.8.1

  Calculations suggest that complexes of borane with N-heterocyclic carbenes (NHC) have B-H bond dissocation energies more then 20 Kcal/mol less than free borane, diborane, borane-THF, and related complexes. Values are in the range of popular radical hydrogen atom donors like tin hydrides (70-80 Kcal/mol). The resulting prediction that NHC borane complexes could be used as radical hydrogen atom donors was verified by radical deoxygenations of xanthates by using either AIBN or triethylborane as initiator.
• Novel radical chain reactions based on O-alkyl tin dithiocarbonates
  作者：Jean Boivin、Jose Camara、Samir Z. Zard

  DOI：10.1021/ja00046a045

  日期：1992.9
• Tetrahydrothiophene nucleosides as potential anti-HIV agents
  作者：Martin F. Jones、Stewart A. Noble、Colin A. Robertson、Richard Storer

  DOI：10.1016/0040-4039(91)80867-6

  日期：1991.1

  A series of novel tetrahydrothiophene nucleosides have been prepared in homochiral form from D-glucose and assessed as anti-HIV agents in whole cell assay.

  已经从D-葡萄糖以同手性形式制备了一系列新的四氢噻吩核苷，并在全细胞测定中被评估为抗HIV药物。
• 3-Deoxy-β-<scp>D</scp>-<i>ribo</i>-hexopyranose (3-deoxy-β-<scp>D</scp>-glucopyranose)
  作者：Wenhui Zhang、Bruce C. Noll、Anthony S. Serianni

  DOI：10.1107/s0108270107038553

  日期：2007.10.15

  The beta- pyranose form, ( III), of 3- deoxy- D- ribo- hexose ( 3- deoxy- D- glucose), C6H12O5, crystallizes from water at 298 K in a slightly distorted C-4(1) chair conformation. Structural analyses of ( III), beta- D- glucopyranose, ( IV), and 2- deoxy- beta- D-arabinohexopyranose ( 2- deoxy- beta- D- glucopyranose), ( V), show significantly different C - O bond torsions involving the anomeric carbon, with the H - C - O - H torsion angle approaching an eclipsed conformation in ( III) (. 10.9 degrees) compared with 32.8 and 32.5 degrees in ( IV) and ( V), respectively. Ring carbon deoxygenation significantly affects the endo- and exocyclic C - C and C - O bond lengths throughout the pyranose ring, with longer bonds generally observed in the monodeoxygenated species ( III) and ( V) compared with ( IV). These structural changes are attributed to differences in exocyclic C - O bond conformations and/ or hydrogenbonding patterns superimposed on the direct ( intrinsic) effect of monodeoxygenation. The exocyclic hydroxymethyl conformation in ( III) ( gt) differs from that observed in ( IV) and ( V) ( gg).