| 1606127-81-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1606127-81-4
• 化学式: C₁₃H₁₅NO₆
• 分子量: 281.265
• InChiKey: RHXNPIKSBIMZFC-WYUUTHIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.68
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  109.9
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 盐酸 、 barium hydroxide octahydrate 、 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 78.25h， 生成
  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：

  (1R,4S,5R,7R)-7-benzyloxy-3-methoxy-5-nitro-2-oxabicyclo[2.2.1]heptane 在 水 、 三氟乙酸 、 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 作用下， 以 水 、 叔丁醇 为溶剂， 反应 5.0h， 生成
  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