(3aR,6R,7S,7aR)-2,2-dimethyl-7-phenylmethoxy-6-(trimethylsilyloxymethyl)-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-amine | 364635-36-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: (3aR,6R,7S,7aR)-2,2-dimethyl-7-phenylmethoxy-6-(trimethylsilyloxymethyl)-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-amine
• CAS: 364635-36-9
• 化学式: C₁₉H₃₁NO₅Si
• 分子量: 381.544
• InChiKey: QWXVZEKSNKNIIT-VXIBKDFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  72.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-硫羰基二咪唑 、 (3aR,6R,7S,7aR)-2,2-dimethyl-7-phenylmethoxy-6-(trimethylsilyloxymethyl)-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-amine 在 四丁基氟化铵 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以83%的产率得到(5R,8R,9R,10S)-1-aza-10-benzyloxy-8,9-dimethylmethylenedioxy-3,6-dioxaspiro[4.5]decan-2-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：

  3-O-benzyl-1,2:4,5-di-O-isopropylidene-β-D-fructopyranose 在 palladium on activated charcoal 叠氮基三甲基硅烷 、 4 A molecular sieve 、 氢气 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.16h， 生成 (3aR,6R,7S,7aR)-2,2-dimethyl-7-phenylmethoxy-6-(trimethylsilyloxymethyl)-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-amine
  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.