methyl 5,7-O-benzylidene-3-deoxy-3-nitro-D-glycero-α-D-ido-heptoseptanoside | 132697-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 5,7-O-benzylidene-3-deoxy-3-nitro-D-glycero-α-D-ido-heptoseptanoside
• CAS: 132697-46-2
• 化学式: C₁₅H₁₉NO₈
• 分子量: 341.318
• InChiKey: YMKDWOQTYIPPCX-PPHWHCQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.16
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  120.52
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl 5,7-O-benzylidene-3-deoxy-3-nitro-D-glycero-α-D-ido-heptoseptanoside 、 乙酰氯 以 溶剂黄146 为溶剂， 以49%的产率得到Acetic acid (2R,4aR,6S,7S,8R,9R,9aS)-7-acetoxy-6-methoxy-8-nitro-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-9-yl ester
  参考文献：
  名称：

  Synthesis of methyl 3-deoxy-3-nitroheptoseptanosides

  摘要：

  The reaction of the dioxepane 2, obtained by periodate oxidation of methyl 4,6-O-benzylidene-alpha-D-glucopyranoside, with nitromethane, using potassium fluoride as catalyst, gave methyl 5,7-O-benzylidene-3-deoxy-3-nitro-D-glycero-alpha-D-ido-heptoseptanoside (2) as the major product. The reaction of 4 with methyl nitroacetate followed by acetylation gave methyl 2,4-di-O-acetyl-5,7-O-benzylidene-3-deoxy-3-C-methoxycarbonyl-3-nitro-D-glycero-alpha-D-talo-(6) and -D-glycero-alpha-D-ido-heptoseptanoside (7).

  DOI：

  10.1016/0008-6215(91)80153-e
• 作为产物：
  描述：

  硝基甲烷 、 (4aR)-7ξ-ethoxy-6c-methoxy-2c-phenyl-(4ar,9at)-hexahydro-[1,3]dioxino[5,4-e][1,4]dioxepin-9ξ-ol 在 potassium fluoride-dibenzo-18-crown-6 ether 作用下， 以 乙腈 为溶剂， 以10%的产率得到(1R,3S,4S,6S,7S,9R)-4-hydroxy-3-methoxy-6-nitromethyl-9-phenyl-2,5,8,10-tetra-oxabicyclo<5,4,0^1,7>undecane
  参考文献：
  名称：

  Synthesis of methyl 3-deoxy-3-nitroheptoseptanosides

  摘要：

  The reaction of the dioxepane 2, obtained by periodate oxidation of methyl 4,6-O-benzylidene-alpha-D-glucopyranoside, with nitromethane, using potassium fluoride as catalyst, gave methyl 5,7-O-benzylidene-3-deoxy-3-nitro-D-glycero-alpha-D-ido-heptoseptanoside (2) as the major product. The reaction of 4 with methyl nitroacetate followed by acetylation gave methyl 2,4-di-O-acetyl-5,7-O-benzylidene-3-deoxy-3-C-methoxycarbonyl-3-nitro-D-glycero-alpha-D-talo-(6) and -D-glycero-alpha-D-ido-heptoseptanoside (7).

  DOI：

  10.1016/0008-6215(91)80153-e