methyl 2,3-di-O-acetyl-4,6-dideoxy-4,6-diiodo-β-D-galactopyranoside | 152733-59-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-acetyl-4,6-dideoxy-4,6-diiodo-β-D-galactopyranoside
• 英文别名: [(2R,3R,4R,5R,6R)-5-acetyloxy-3-iodo-2-(iodomethyl)-6-methoxyoxan-4-yl] acetate
• CAS: 152733-59-0
• 化学式: C₁₁H₁₆I₂O₆
• 分子量: 498.053
• InChiKey: PRXVAGDMSCOQEV-ZKKRXERASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-acetyl-4,6-dideoxy-4,6-diiodo-β-D-galactopyranoside 在 palladium on activated charcoal 氢气 、 二乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以56%的产率得到methyl 2,3-di-O-acetyl-4,6-cyclo-4,6-dideoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Preparation of 4,6-cyclo-4,6-dideoxy-hexopyranoses by palladium-mediated intramolecular cyclodehalogenation

  摘要：

  4,6-Cyclo-4,6-dideoxy-hexopyranoses were obtained by palladium-mediated intramolecular cyclodehalogenation. Thus, methyl 2,3-di-O-acetyl-4,6-dideoXY-4,6-diiodo-beta-D-galactopyranoside (3) afforded methyl 2,3-di-O-acetyl-4,6-cyclo-4,6-dideoxy-beta-D-galactopyranoside (5) in 56% yield upon treatment with hydrogen in the presence of palladium-on-charcoal and diethylamine. The structure of 5 was proven by MS, NMR including NOE measurements, and by independent conversion of 4 to 5 by zinc-mediated Wurtz synthesis. Similarly, methyl 2,3-di-O-acetyl-4,6-cyclo-4,6-dideoxy-alpha-D-galactopyranoside (6) and O-(2,3-di-O-acetyl-4,6-cyclo-4,6-dideoxy-alpha-D-galactopyranosyl)-(l --> 4)-1,2,3,6-tetra-0-acetyl-beta-D-glucopyranose (17) were obtained along with the respective 4,6-dideoxy analogues. Also methyl 2,3-di-O-acetyl-4,6-dideoxy-4,6-diiodo-beta-D-glucopyranoside (19) gave galacto-configured 5 stereoselectively.

  DOI：

  10.1016/0008-6215(93)80074-o
• 作为产物：
  描述：

  Methyl 2,3-di-O-acetyl-β-D-glucopyranoside 在 咪唑 、 碘 、 三苯基膦 作用下， 以 甲苯 、 乙腈 为溶剂， 以95%的产率得到methyl 2,3-di-O-acetyl-4,6-dideoxy-4,6-diiodo-β-D-galactopyranoside
  参考文献：
  名称：

  Preparation of 4,6-cyclo-4,6-dideoxy-hexopyranoses by palladium-mediated intramolecular cyclodehalogenation

  摘要：

  4,6-Cyclo-4,6-dideoxy-hexopyranoses were obtained by palladium-mediated intramolecular cyclodehalogenation. Thus, methyl 2,3-di-O-acetyl-4,6-dideoXY-4,6-diiodo-beta-D-galactopyranoside (3) afforded methyl 2,3-di-O-acetyl-4,6-cyclo-4,6-dideoxy-beta-D-galactopyranoside (5) in 56% yield upon treatment with hydrogen in the presence of palladium-on-charcoal and diethylamine. The structure of 5 was proven by MS, NMR including NOE measurements, and by independent conversion of 4 to 5 by zinc-mediated Wurtz synthesis. Similarly, methyl 2,3-di-O-acetyl-4,6-cyclo-4,6-dideoxy-alpha-D-galactopyranoside (6) and O-(2,3-di-O-acetyl-4,6-cyclo-4,6-dideoxy-alpha-D-galactopyranosyl)-(l --> 4)-1,2,3,6-tetra-0-acetyl-beta-D-glucopyranose (17) were obtained along with the respective 4,6-dideoxy analogues. Also methyl 2,3-di-O-acetyl-4,6-dideoxy-4,6-diiodo-beta-D-glucopyranoside (19) gave galacto-configured 5 stereoselectively.

  DOI：

  10.1016/0008-6215(93)80074-o