octyl 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-iodo-α-D-mannopyranoside | 219825-31-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: octyl 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-iodo-α-D-mannopyranoside
• CAS: 219825-31-7
• 化学式: C₃₂H₄₉IO₁₆
• 分子量: 816.636
• InChiKey: BSFRIMPGWNDHDO-QINZEGFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  49.0
• 可旋转键数：
  18.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  194.72
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  octyl 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-iodo-α-D-mannopyranoside 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 3.0h， 以91%的产率得到octyl 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  Iodoacetoxylation Reaction: A Convenient Route to α-Glycosides in the 2-Iodo and 2-Deoxy Series

  摘要：

  Iodoacetoxylation of 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (tri-O-acetyl-D-glucal)(1) and 3,4-di-O-acetyl-1,5-anhydro-2,6-dideoxy-L-arabino-hex-1-enitol (di-O-acetyl-L-rhamnal) (3) gave the alpha-1,2-trans-1-O-acetyl-2-deoxy-2-iodo adducts with high stereoselectivities and good yields, in accordance with the results reported on 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-1,5-anhydro-2-deoxy-D-arahino-hex-1-enitol (hexa-O-acetyl lactal) (2). The alpha-1,2-trans adducts were reacted with an excess of alcohol in the presence of trimethylsilyl trifluoromethanesulfonate affording the corresponding alpha-1,2-trans-2-deoxy-2-iodo-glycopyranoside in good yields. The octyl 2-deoxy-2-iodo-alpha-D-glycosides 10 and 11 prepared in two steps from the glycals 1 and 2 were deiodinated and deacetylated, giving 28 and 29, and the physicochemical-properties (cmc) of 29 are reported.

  DOI：

  10.1080/07328309808002360
• 作为产物：
  描述：

  三甲基(辛氧基)硅烷 、 1,3,6-tri-O-acetyl-4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-iodo-α-D-manno-pyranose 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到octyl 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-iodo-α-D-mannopyranoside
  参考文献：
  名称：

  Iodoacetoxylation Reaction: A Convenient Route to α-Glycosides in the 2-Iodo and 2-Deoxy Series

  摘要：

  Iodoacetoxylation of 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (tri-O-acetyl-D-glucal)(1) and 3,4-di-O-acetyl-1,5-anhydro-2,6-dideoxy-L-arabino-hex-1-enitol (di-O-acetyl-L-rhamnal) (3) gave the alpha-1,2-trans-1-O-acetyl-2-deoxy-2-iodo adducts with high stereoselectivities and good yields, in accordance with the results reported on 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-1,5-anhydro-2-deoxy-D-arahino-hex-1-enitol (hexa-O-acetyl lactal) (2). The alpha-1,2-trans adducts were reacted with an excess of alcohol in the presence of trimethylsilyl trifluoromethanesulfonate affording the corresponding alpha-1,2-trans-2-deoxy-2-iodo-glycopyranoside in good yields. The octyl 2-deoxy-2-iodo-alpha-D-glycosides 10 and 11 prepared in two steps from the glycals 1 and 2 were deiodinated and deacetylated, giving 28 and 29, and the physicochemical-properties (cmc) of 29 are reported.

  DOI：

  10.1080/07328309808002360