(2R,3R,4R,5S)-6-aza-2-benzyloxymethyl-3,4-dimethylmethylenedioxy-1,8-dioxaspiro[4.4]nonan-7-thione | 364635-28-9

• 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: (2R,3R,4R,5S)-6-aza-2-benzyloxymethyl-3,4-dimethylmethylenedioxy-1,8-dioxaspiro[4.4]nonan-7-thione
• 英文别名: (3'aR,4S,6'R,6'aR)-2',2'-dimethyl-6'-(phenylmethoxymethyl)spiro[1,3-oxazolidine-4,4'-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole]-2-thione
• CAS: 364635-28-9
• 化学式: C₁₇H₂₁NO₅S
• 分子量: 351.423
• InChiKey: ZPMNUACFECNMHG-WBOJAVRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  90.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S)-6-aza-2-benzyloxymethyl-3,4-dimethylmethylenedioxy-1,8-dioxaspiro[4.4]nonan-7-thione 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以80%的产率得到(2R,3R,4R,5R)-6-aza-2-benzyloxymethyl-3,4-dimethylmethylenedioxy-1,8-dioxaspiro[4,4]nonan-7-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：

  ((3aR,4R,6R,6aR)-4-Azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-trimethyl-silane 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 (2R,3R,4R,5S)-6-aza-2-benzyloxymethyl-3,4-dimethylmethylenedioxy-1,8-dioxaspiro[4.4]nonan-7-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

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.