2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl 1-(methylenediphosphonate) | 108946-21-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl 1-(methylenediphosphonate)
• 英文别名: [hydroxy-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyphosphoryl]methylphosphonic acid
• CAS: 108946-21-0
• 化学式: C₁₅H₂₄O₁₅P₂
• 分子量: 506.294
• InChiKey: NXLGGGSVKBJXPI-GZBLMMOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.59
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  218.49
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl 1-(methylenediphosphonate) 在 ammonium hydroxide 作用下， 反应 1.0h， 生成 α-D-galactopyranosyl 1-(methylenediphosphonate) ammonium salt
  参考文献：
  名称：

  Synthesis of certain nucleoside methylenediphosphonate sugars as potential inhibitors of glycosyltransferases

  摘要：

  The synthesis of alpha-D-glucopyranosyl 1-(methylenediphosphonate) (11), alpha-D-galactopyranosyl 1-(methylenediphosphonate) (14), and alpha-D-mannopyranosyl 1-(methylenediphosphonate) (17) has been accomplished. [(Di-phenoxyphosphinyl)methyl]phosphonic acid (diphenyl-MDP) (5), synthesized by two different procedures, was fused with beta-D-glucopyranose pentaacetate followed by catalytic hydrogenation to give 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl methylenediphosphonate (glucose-MDP) (10). The anomeric configuration of 10 was assigned on the basis of NMR spectral studies. Condensation of 10 with 2',3'-di-O-acetyladenosine was accomplished by using 1-(mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole (MSNT) as coupling agent, and removal of the blocking groups gave adenosine 5'-[(alpha-D-glucopyranosylhydroxyphosphinyl)methyl]phosphonate (20). Uridine 5'-[(alpha-D-galactopyranosylhydroxyphosphinyl)methyl] phosphonate (23) and guanosine 5'-[(alpha-D-mannopyranosylhydroxyphosphinyl)methyl]phosphonate (26) were similarly prepared. Using a specific glycoprotein galactosyltransferase (EC 2.4.1.38) assay, uridine 5'-[(alpha-D-galactopyranosylhydroxyphosphinyl)methyl]phosphonate (23) demonstrated competitive inhibition with an apparent Ki of 97 microM. The adenosine analogue did not inhibit the enzyme. None of the above compounds show any in vitro antitumor or antiviral activity. Such specific inhibitors of glycosyltransferases may serve as specific probes to study various glycosyltransferases that might be involved in the process of metastasis.

  DOI：

  10.1021/jm00391a021
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl 1-<<(diphenoxyphosphinyl)methyl>phosphonate> 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 为溶剂， 40.0 ℃ 、6.89 MPa 条件下， 生成 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl 1-(methylenediphosphonate)
  参考文献：
  名称：

  Synthesis of certain nucleoside methylenediphosphonate sugars as potential inhibitors of glycosyltransferases

  摘要：

  The synthesis of alpha-D-glucopyranosyl 1-(methylenediphosphonate) (11), alpha-D-galactopyranosyl 1-(methylenediphosphonate) (14), and alpha-D-mannopyranosyl 1-(methylenediphosphonate) (17) has been accomplished. [(Di-phenoxyphosphinyl)methyl]phosphonic acid (diphenyl-MDP) (5), synthesized by two different procedures, was fused with beta-D-glucopyranose pentaacetate followed by catalytic hydrogenation to give 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl methylenediphosphonate (glucose-MDP) (10). The anomeric configuration of 10 was assigned on the basis of NMR spectral studies. Condensation of 10 with 2',3'-di-O-acetyladenosine was accomplished by using 1-(mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole (MSNT) as coupling agent, and removal of the blocking groups gave adenosine 5'-[(alpha-D-glucopyranosylhydroxyphosphinyl)methyl]phosphonate (20). Uridine 5'-[(alpha-D-galactopyranosylhydroxyphosphinyl)methyl] phosphonate (23) and guanosine 5'-[(alpha-D-mannopyranosylhydroxyphosphinyl)methyl]phosphonate (26) were similarly prepared. Using a specific glycoprotein galactosyltransferase (EC 2.4.1.38) assay, uridine 5'-[(alpha-D-galactopyranosylhydroxyphosphinyl)methyl]phosphonate (23) demonstrated competitive inhibition with an apparent Ki of 97 microM. The adenosine analogue did not inhibit the enzyme. None of the above compounds show any in vitro antitumor or antiviral activity. Such specific inhibitors of glycosyltransferases may serve as specific probes to study various glycosyltransferases that might be involved in the process of metastasis.

  DOI：

  10.1021/jm00391a021

文献信息

• VAGHEFI, M. M.;BERNACKI, R. J.;HENNEN, W. J.;ROBINS, R. K., J. MED. CHEM., 30,(1987) N 8, 1391-1399
  作者：VAGHEFI, M. M.、BERNACKI, R. J.、HENNEN, W. J.、ROBINS, R. K.

  DOI：——

  日期：——