2-[((2R,3R,4S,5R)-3,4,5-Tris-methanesulfonyloxy-tetrahydro-pyran-2-ylamino)-methylene]-malonic acid diethyl ester | 198640-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-[((2R,3R,4S,5R)-3,4,5-Tris-methanesulfonyloxy-tetrahydro-pyran-2-ylamino)-methylene]-malonic acid diethyl ester
• 英文别名: diethyl 2-[[[(2R,3R,4S,5R)-3,4,5-tris(methylsulfonyloxy)oxan-2-yl]amino]methylidene]propanedioate
• CAS: 198640-89-0
• 化学式: C₁₆H₂₇NO₁₄S₃
• 分子量: 553.587
• InChiKey: DLHLMDIMZBUEGB-XJFOESAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  229
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2-[((2R,3R,4S,5R)-3,4,5-Tris-methanesulfonyloxy-tetrahydro-pyran-2-ylamino)-methylene]-malonic acid diethyl ester 在 六甲基磷酰三胺 、 sodium methylate 、 三氟乙酸 作用下， 反应 16.17h， 生成 2-[((3S,4S,5R,6S)-6-Hydroxy-4,5-bis-methanesulfonyloxy-tetrahydro-pyran-3-ylamino)-methylene]-malonic acid diethyl ester
  参考文献：
  名称：

  Stereoselective syntheses of 4-amino-aldoses, and chiral pyrrolidine derivatives from glycosylenamines

  摘要：

  The stereocontrolled synthesis of N-protected 4-amino-4-deoxy-D-galacto- and -L-arabino-pyranoses starting from glycosylenamines via aza-anhydropyranoses is described. The steroselective transformation of the intermediate aza-anhydropyranoses into chiral pyrrolidines is also reported. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00404-7
• 作为产物：
  描述：

  N-[1-(2,2-diethoxycarbonylvinyl)]-β-D-xylopyranosylamine 、 甲基磺酰氯 在 吡啶 作用下， 反应 24.0h， 以71%的产率得到2-[((2R,3R,4S,5R)-3,4,5-Tris-methanesulfonyloxy-tetrahydro-pyran-2-ylamino)-methylene]-malonic acid diethyl ester
  参考文献：
  名称：

  Stereoselective syntheses of 4-amino-aldoses, and chiral pyrrolidine derivatives from glycosylenamines

  摘要：

  The stereocontrolled synthesis of N-protected 4-amino-4-deoxy-D-galacto- and -L-arabino-pyranoses starting from glycosylenamines via aza-anhydropyranoses is described. The steroselective transformation of the intermediate aza-anhydropyranoses into chiral pyrrolidines is also reported. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00404-7

文献信息

• Rearrangements of O-protected glycosylenamines. A new and efficient route for the synthesis of O-protected 4-aminoaldoses
  作者：M Angeles Pradera、David Olano、José Fuentes

  DOI：10.1016/0040-4039(95)01737-3

  日期：1995.11

  O-Protected 4-deoxy -4-diethoxycarbonylaminoaldoses with D-galacto. I.-arabino and I-lyxo contigurations (3) are prepared by a nucleophilic rearrangement of easily available glycosylamine derivatives

  O-保护的带有D-半乳糖的4-脱氧-4-二乙氧基羰基氨基醛糖。余。阿拉伯糖和我-lyxo contigurations（3）由容易获得的糖基胺衍生物的亲核重排制备