((3aR,4S,6R,6aR)-6-Benzyloxymethyl-4-isothiocyanatomethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methanol | 364635-30-3

• 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: ((3aR,4S,6R,6aR)-6-Benzyloxymethyl-4-isothiocyanatomethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methanol
• 英文别名: [(3aR,4S,6R,6aR)-4-(isothiocyanatomethyl)-2,2-dimethyl-6-(phenylmethoxymethyl)-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]methanol
• CAS: 364635-30-3
• 化学式: C₁₈H₂₃NO₅S
• 分子量: 365.45
• InChiKey: KKVRMVLLHYERJU-KONPQCLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ((3aR,4S,6R,6aR)-6-Benzyloxymethyl-4-isothiocyanatomethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methanol 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以96%的产率得到(2R,3R,4R,5S)-9-aza-2-benzyloxymethyl-3,4-dimethylmethylenedioxy-1,7-dioxaspiro[4.5]decane-8-thione
  参考文献：
  名称：

  Isothiocyanato derivatives of sugars in the stereoselective synthesis of spironucleosides and spiro-C-glycosides

  摘要：

  A stereocontrolled synthesis of pyranoid and furanoid spironucleosides and spiro-C-glycosides (D-ribo and D-arabino configurations) of oxazolidines, oxazolines and perhydrooxazines via isothiocyanato sugar derivatives is reported. The intermediate isothiocyanates are prepared from sugar spiroketals by stereoselective opening of the acetal ring with trimethylsilyl N- and C-nucleophiles, and later formation of the isothiocyanato group. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00223-3
• 作为产物：
  描述：

  6-O-benzyl-3,4-O-isopropylidene-α-D-psicofuranosyl cyanide 在 lithium aluminium tetrahydride 、 水 、 calcium carbonate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 ((3aR,4S,6R,6aR)-6-Benzyloxymethyl-4-isothiocyanatomethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methanol
  参考文献：
  名称：

  Isothiocyanato derivatives of sugars in the stereoselective synthesis of spironucleosides and spiro-C-glycosides

  摘要：

  A stereocontrolled synthesis of pyranoid and furanoid spironucleosides and spiro-C-glycosides (D-ribo and D-arabino configurations) of oxazolidines, oxazolines and perhydrooxazines via isothiocyanato sugar derivatives is reported. The intermediate isothiocyanates are prepared from sugar spiroketals by stereoselective opening of the acetal ring with trimethylsilyl N- and C-nucleophiles, and later formation of the isothiocyanato group. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00223-3

文献信息

• Isothiocyanato derivatives of sugars in the stereoselective synthesis of spironucleosides and spiro-C-glycosides
  作者：Consolación Gasch、M.Angeles Pradera、Bader A.B. Salameh、José L. Molina、José Fuentes

  DOI：10.1016/s0957-4166(01)00223-3

  日期：2001.6

  A stereocontrolled synthesis of pyranoid and furanoid spironucleosides and spiro-C-glycosides (D-ribo and D-arabino configurations) of oxazolidines, oxazolines and perhydrooxazines via isothiocyanato sugar derivatives is reported. The intermediate isothiocyanates are prepared from sugar spiroketals by stereoselective opening of the acetal ring with trimethylsilyl N- and C-nucleophiles, and later formation of the isothiocyanato group. (C) 2001 Elsevier Science Ltd. All rights reserved.