methyl 2,5-anhydro-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptonate | 145372-67-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,5-anhydro-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptonate
• 英文别名: methyl (3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate
• CAS: 145372-67-4
• 化学式: C₁₄H₂₂O₇
• 分子量: 302.324
• InChiKey: ULKMOMURHJZLPA-UVOCVTCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,5-anhydro-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptonate 在 吡啶 、 lithium aluminium tetrahydride 、 sodium azide 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.83h， 生成 (3aR,4R,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylperhydrofuro[3,4-d][1,3]dioxol-4-yl-methyl azide
  参考文献：
  名称：

  Inhibition of α-mannosidases by seven carbon sugars: Synthesis of some seven carbon analogues of mannofuranose

  摘要：

  The effects on human liver glycosidases of some seven carbon analogues of mannopyranose and mannofuranose are compared with those of deoxymannojirimycin and DIM. The syntheses of the seven carbon mannofuranose analogues, alpha-(aminomethyl)-1-deoxy-mannofuranose and of alpha-homoDIM, are described.

  DOI：

  10.1016/s0040-4020(01)89046-3
• 作为产物：
  描述：

  3,4:6,7-di-O-isopropylidene-2-O-trifluoromethanesulphonyl-D-glycero-D-talo-heptono-1,5-lactone 在 四丁基碘化铵 、 potassium carbonate 作用下， 反应 4.0h， 生成 methyl 2,5-anhydro-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptonate
  参考文献：
  名称：

  Inhibition of α-mannosidases by seven carbon sugars: Synthesis of some seven carbon analogues of mannofuranose

  摘要：

  The effects on human liver glycosidases of some seven carbon analogues of mannopyranose and mannofuranose are compared with those of deoxymannojirimycin and DIM. The syntheses of the seven carbon mannofuranose analogues, alpha-(aminomethyl)-1-deoxy-mannofuranose and of alpha-homoDIM, are described.

  DOI：

  10.1016/s0040-4020(01)89046-3

文献信息

• The ring contraction of δ-lactones with leaving group α-substituents: a strategy for the synthesis of 2,5-disubstituted highly functionalised homochiral tetrahydrofurans
  作者：Sik-Man S. Choi、Paul M. Myerscough、Antony J. Fairbanks、Ben M. Skead、Claire J. F. Bichard、Simon J. Mantell、Jong Chan Son、George W. J. Fleet、John Saunders、David Brown

  DOI：10.1039/c39920001605

  日期：——

  Treatment of derivatives of δ-lactones having a leaving group at C-2 with methanol in the presence of base gives methyl tetrahydrofuran-α-carboxylates in good to excellent yield with a high degree of stereocontrol of the carbon substituents at C-2 and C-5.

  在碱存在下，用甲醇处理C-2位带有保护基的γ-内酯衍生物，可以得到甲基四氢呋喃-γ-羧酸酯，收率良好到极佳，且C-2和C-5位碳取代基具有高度的立体选择性。
• Furan-based synthesis of C-glycosyl carboxylates
  作者：Alessandro Dondoni、Alberto Marra、Marie-Christine Scherrmann

  DOI：10.1016/s0040-4039(00)79320-8

  日期：1993.11

  The installation of the 2-furyl ring at the anomeric carbon of 2,3,4,6-tetra-O-benzyl-D-glucopyranose and 2,3.5,6-di-O-isopropylidene-D-mannofuranose is carried out either by addition of 2-lithiofuran to the corresponding lactones either by direct C-glycosidation of the O-acetyl derivatives with furan; the resultant 2-furyl C-glycosides are converted to carboxylic acids by the oxidative cleavage of the furan nucleous.