methyl (2-(((3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)acetyl)-L-alaninate | 1078159-43-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2-(((3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)acetyl)-L-alaninate
• CAS: 1078159-43-9
• 化学式: C₁₈H₂₉NO₉
• 分子量: 403.43
• InChiKey: CJEXXTYTONXEQP-AILALQLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.08
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  110.78
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl (2-(((3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)acetyl)-L-alaninate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以92%的产率得到2-(((3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-N-((S)-1-hydrazineyl-1-oxopropan-2-yl)acetamide
  参考文献：
  名称：

  Amino Acid Derivatives, V [1]: Synthesis and Antiviral Evaluation of α-Amino Acid Esters Bearing an α-d-Mannofuranoside Side Chain

  摘要：

  D-Mannose was treated with dry acetone in the presence of conc. H2SO4 to afford 2,3:5,6-di-O-isopropylidene-alpha-D-mannofuranoside. Treating the latter with ethyl chloroacetate gave carboethoxymethyl 2,3:5,6-di-O-isopropylidene-alpha-D-mannofuranoside, which was hydrolyzed with N2H4 center dot H2O to afford the acid hydrazide derivative. Treating of the acid hydrazide with acylated amino acides, via the azide-coupling method afforded the corresponding O-glycopeptides. Reaction of the glycopeptide methyl esters with N2H4 center dot H2O afforded the corresponding hydrazides, which were coupled with the amino acid methyl esters to afford the dipeptides. Deprotection was carried out by using 70% AcOH. The prepared O-glycopeptides were tested for antiviral activity against hepatitis B virus and showed moderate activities.

  DOI：

  10.1007/s00706-007-0734-y
• 作为产物：
  描述：

  2-(((3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)acetohydrazide 、 L-丙氨酸甲酯盐酸盐 在 盐酸 、 sodium nitrite 、 三乙胺 作用下， 以 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 0.25h， 以80%的产率得到methyl (2-(((3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)acetyl)-L-alaninate
  参考文献：
  名称：

  Amino Acid Derivatives, V [1]: Synthesis and Antiviral Evaluation of α-Amino Acid Esters Bearing an α-d-Mannofuranoside Side Chain

  摘要：

  D-Mannose was treated with dry acetone in the presence of conc. H2SO4 to afford 2,3:5,6-di-O-isopropylidene-alpha-D-mannofuranoside. Treating the latter with ethyl chloroacetate gave carboethoxymethyl 2,3:5,6-di-O-isopropylidene-alpha-D-mannofuranoside, which was hydrolyzed with N2H4 center dot H2O to afford the acid hydrazide derivative. Treating of the acid hydrazide with acylated amino acides, via the azide-coupling method afforded the corresponding O-glycopeptides. Reaction of the glycopeptide methyl esters with N2H4 center dot H2O afforded the corresponding hydrazides, which were coupled with the amino acid methyl esters to afford the dipeptides. Deprotection was carried out by using 70% AcOH. The prepared O-glycopeptides were tested for antiviral activity against hepatitis B virus and showed moderate activities.

  DOI：

  10.1007/s00706-007-0734-y