(4R,5R)-2-{(2S,4R,5S,6R)-5-azido-2-[(benzyloxy)methyl]-3,4,5,6-tetrahydro-4-[(triethylsilyl)oxy]-6-{[(triisopropylsilyl)oxy]methyl}-2H-pyran-2-yl}-4,5-diphenylimidazolidine | 330808-18-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (4R,5R)-2-{(2S,4R,5S,6R)-5-azido-2-[(benzyloxy)methyl]-3,4,5,6-tetrahydro-4-[(triethylsilyl)oxy]-6-{[(triisopropylsilyl)oxy]methyl}-2H-pyran-2-yl}-4,5-diphenylimidazolidine
• 英文别名: [(2R,3S,4R,6S)-3-azido-6-[(4R,5R)-4,5-diphenylimidazolidin-2-yl]-6-(phenylmethoxymethyl)-4-triethylsilyloxyoxan-2-yl]methoxy-tri(propan-2-yl)silane
• CAS: 330808-18-9
• 化学式: C₄₄H₆₇N₅O₄Si₂
• 分子量: 786.218
• InChiKey: KGDGVTBMHUNZQT-VAODMJBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.99
• 重原子数：
  55
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  75.3
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4R,5R)-2-{(2S,4R,5S,6R)-5-azido-2-[(benzyloxy)methyl]-3,4,5,6-tetrahydro-4-[(triethylsilyl)oxy]-6-{[(triisopropylsilyl)oxy]methyl}-2H-pyran-2-yl}-4,5-diphenylimidazolidine 在 盐酸 作用下， 以 乙醚 为溶剂， 以95%的产率得到(2RS,4RS,5SR,6RS)-2,6-anhydro-5-azido-2-C-[(benzyloxy)methyl]-3,5-dideoxy-4-O-triethylsilyl-7-O-triisopropylsilyl-DL-allo-heptose
  参考文献：
  名称：

  Total synthesis of a protected form of 2,6-anhydro-5-azido-3,5-dideoxy-2-C-hydroxymethyl-l-allo-heptose; a potential precursor of analogs of C-glycosides of neuraminic acid

  摘要：

  The title aldehyde (-)-3 and its enantiomer (+)-3 have been prepared starting from furfuryl alcohol and acetone. The method involves the diastereoselective [4+3]-cycloaddition of 2-[(benzyloxy)methyl]furan and 1, 3-dibromo-2-oxyallyl cation giving adduct (+/-)-4 that was converted with high yield into (+)(2RS, 5RS, 6SR)- 5-azido -2-[(benzyloxy)methyl] -2, 3,5,6-tetrahydro-2, 6-bis (hydroxymethyl) -4H-pyran-4-one ((+/-)-9). Ketone (+/-)-9 was then transformed with high selectivity into (+/-)-(2RS,4RS,5SR,6RS)-5-azido-2-[(benzyloxy)methyl]-2, 3,5,6-tetrahydro-4-[(triethylsilyl)oxy]-6-{[(triisopropylsilyl)oxy]methyl}-2H-pyran-2-methanol (+)-3 that was resolved by the Alexakis-Mangeney method (column chromatography of aminals derived from (1R,2R)-1,2-diphenylethylenediamine). The absolute configuration of (-)-3 was established by circular dichroism and the Dale-Mosher method on derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00460-2
• 作为产物：
  描述：

  (2RS,3SR,4SR,5SR,6RS)-2-[(benzyloxy)methyl]-3,5-dibromo-3,4,5,6-tetrahydro-4-(methoxymethoxy)-2H-pyran-2,6-dimethanol 在 吡啶 、 咪唑 、 盐酸 、 六甲基磷酰三胺 、 sodium tetrahydroborate 、 sodium azide 、 4 A molecular sieve 、 potassium carbonate 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 190.17h， 生成 (4R,5R)-2-{(2S,4R,5S,6R)-5-azido-2-[(benzyloxy)methyl]-3,4,5,6-tetrahydro-4-[(triethylsilyl)oxy]-6-{[(triisopropylsilyl)oxy]methyl}-2H-pyran-2-yl}-4,5-diphenylimidazolidine
  参考文献：
  名称：

  Total synthesis of a protected form of 2,6-anhydro-5-azido-3,5-dideoxy-2-C-hydroxymethyl-l-allo-heptose; a potential precursor of analogs of C-glycosides of neuraminic acid

  摘要：

  The title aldehyde (-)-3 and its enantiomer (+)-3 have been prepared starting from furfuryl alcohol and acetone. The method involves the diastereoselective [4+3]-cycloaddition of 2-[(benzyloxy)methyl]furan and 1, 3-dibromo-2-oxyallyl cation giving adduct (+/-)-4 that was converted with high yield into (+)(2RS, 5RS, 6SR)- 5-azido -2-[(benzyloxy)methyl] -2, 3,5,6-tetrahydro-2, 6-bis (hydroxymethyl) -4H-pyran-4-one ((+/-)-9). Ketone (+/-)-9 was then transformed with high selectivity into (+/-)-(2RS,4RS,5SR,6RS)-5-azido-2-[(benzyloxy)methyl]-2, 3,5,6-tetrahydro-4-[(triethylsilyl)oxy]-6-{[(triisopropylsilyl)oxy]methyl}-2H-pyran-2-methanol (+)-3 that was resolved by the Alexakis-Mangeney method (column chromatography of aminals derived from (1R,2R)-1,2-diphenylethylenediamine). The absolute configuration of (-)-3 was established by circular dichroism and the Dale-Mosher method on derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00460-2