carbethoxymethyl 2,3:5,6-di-O-isopropylidene-α-D-mannofuranoside | 1078159-37-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: carbethoxymethyl 2,3:5,6-di-O-isopropylidene-α-D-mannofuranoside
• CAS: 1078159-37-1
• 化学式: C₁₆H₂₆O₈
• 分子量: 346.378
• InChiKey: OYBWKIGGASLJFC-CYDRSHDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  carbethoxymethyl 2,3:5,6-di-O-isopropylidene-α-D-mannofuranoside 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以95%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)acetohydrazide
  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：

  氯乙酸乙酯 、 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以80%的产率得到carbethoxymethyl 2,3:5,6-di-O-isopropylidene-α-D-mannofuranoside
  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