| 1606127-85-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1606127-85-8
• 化学式: C₃₂H₄₀O₅Si
• 分子量: 532.752
• InChiKey: XJNHQEPLEXSZTQ-MIPYOGIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 吡啶 、 间苯三酚 、 四丁基氟化铵 、 水 、 溴 、 barium carbonate 、 三氟乙酸 、 sodium iodide 、 sodium nitrite 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 二甲基亚砜 、 丙酮 为溶剂， 反应 144.5h， 生成 5-O-benzyl-3,6-dideoxy-6-nitro-2-O-trifluoromethanesulphonyl-D-glucono-1,4-lactone
  参考文献：
  名称：

  Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. Part 6: synthesis and incorporation into peptides of the first reported 2,3-dihydroxycyclopentanecarboxylic acid

  摘要：

  Herein we report the intramolecular alkylation of nitronates of methyl-5-O-benzy1-3,6-deoxy-6-nitro-alpha-D-glucofuranoside and methyl-5-O-benzyl-3,6-deoxy-6-nitro-alpha-D-glucofuranoside into the corresponding 2-oxabicyclo[2.2.1]heptane derivatives. Similarly, methyl-3-O-benzy1-5-deoxy-5-nitromethy1-13-beta-D-xylofuranoside and methyl-3-O-benzyl-5-deoxy-5-nitromethyl-alpha-D-xylofuranoside were cyclized to (1R,3R, 45,5R,7R)-7-benzyloxy-3-methoxy-5-nitro-2-oxabicyclo[2.2.1]heptane and (1R,3S,4S,5R,7R)-7-benzyloxy-3-methoxy-5-nitro-2-oxabicyclo[2.2.1]heptane, respectively. These 2-oxabicyclo[2.2.1]heptane derivatives were eventually transformed into enantiopure methyl (15,2S,3R,4S,5R)-2-amino-2,3-dihydroxycyclopentanecarboxylate and this novel beta-amino acid was incorporated into peptides. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.03.005
• 作为产物：
  描述：

  溴甲苯 、 6-O-tert-butyldiphenylsilyl-3-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose 在 四丁基碘化铵 、 sodium hydride 、 甲醇 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以63%的产率得到
  参考文献：
  名称：

  Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. Part 6: synthesis and incorporation into peptides of the first reported 2,3-dihydroxycyclopentanecarboxylic acid

  摘要：

  Herein we report the intramolecular alkylation of nitronates of methyl-5-O-benzy1-3,6-deoxy-6-nitro-alpha-D-glucofuranoside and methyl-5-O-benzyl-3,6-deoxy-6-nitro-alpha-D-glucofuranoside into the corresponding 2-oxabicyclo[2.2.1]heptane derivatives. Similarly, methyl-3-O-benzy1-5-deoxy-5-nitromethy1-13-beta-D-xylofuranoside and methyl-3-O-benzyl-5-deoxy-5-nitromethyl-alpha-D-xylofuranoside were cyclized to (1R,3R, 45,5R,7R)-7-benzyloxy-3-methoxy-5-nitro-2-oxabicyclo[2.2.1]heptane and (1R,3S,4S,5R,7R)-7-benzyloxy-3-methoxy-5-nitro-2-oxabicyclo[2.2.1]heptane, respectively. These 2-oxabicyclo[2.2.1]heptane derivatives were eventually transformed into enantiopure methyl (15,2S,3R,4S,5R)-2-amino-2,3-dihydroxycyclopentanecarboxylate and this novel beta-amino acid was incorporated into peptides. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.03.005