(2S,3R,4R,5R)-2-methoxy-5-(2-nitroethyl)-4-phenylmethoxyoxolan-3-ol | 1606127-97-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5R)-2-methoxy-5-(2-nitroethyl)-4-phenylmethoxyoxolan-3-ol
• CAS: 1606127-97-2
• 化学式: C₁₄H₁₉NO₆
• 分子量: 297.308
• InChiKey: IBNJDUBWENGPSQ-MQYQWHSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  93.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲醇 、 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-6-C-nitro-α-D-xylo-hexanofuranose 在 乙酰氯 作用下， 反应 14.0h， 以44%的产率得到(2R,3R,4R,5R)-2-methoxy-5-(2-nitroethyl)-4-phenylmethoxyoxolan-3-ol
  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