(3aR,6R,7S,7aR)-6-(hydroxymethyl)-2,2-dimethyl-7-phenylmethoxy-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbonitrile | 364635-38-1

• 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)-6-(hydroxymethyl)-2,2-dimethyl-7-phenylmethoxy-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbonitrile
• CAS: 364635-38-1
• 化学式: C₁₇H₂₁NO₅
• 分子量: 319.357
• InChiKey: RRIAHSNDQISSFF-PNBKFKSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  80.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aR,6R,7S,7aR)-6-(hydroxymethyl)-2,2-dimethyl-7-phenylmethoxy-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbonitrile 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (3R,4R,5S,6R)-10-aza-5-benzyloxy-3,4-dimethylmethylenedioxy-1,8-dioxaspiro[5.5]undecan-9-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 4 A molecular sieve 、 四丁基氟化铵 作用下， 以 二氯甲烷 为溶剂， 反应 13.08h， 生成 (3aR,6R,7S,7aR)-6-(hydroxymethyl)-2,2-dimethyl-7-phenylmethoxy-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbonitrile
  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

• Expeditious synthesis of sulfoazetidine spiro-C-glycosides from ketose acetals
  作者：Francisco J. Sayago、M. Ángeles Pradera、Consolación Gasch、José Fuentes

  DOI：10.1016/j.tet.2005.10.038

  日期：2006.1

  Pyranoid and furanoid spiro-N-mesyl azetidines, a new type of water-soluble spiro-C-nucleoside, have been prepared from easily available sugar spiroacetals (or glycosyl cyanides). The synthetic pathway involves opening of the acetalic ring with trimethylsilylcyanide, reduction, formation of an N,O-dimesylate, cyclization with sodium hydride in anhydrous DMF, and O-deprotection. (c) 2005 Elsevier Ltd. All rights reserved.
• 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.