[(3aR,5R,6R,7S,7aR)-6,7-diacetyloxy-2-bis(phenylmethoxy)phosphoryl-2-methyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl acetate | 153658-88-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(3aR,5R,6R,7S,7aR)-6,7-diacetyloxy-2-bis(phenylmethoxy)phosphoryl-2-methyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl acetate
• CAS: 153658-88-9
• 化学式: C₂₈H₃₃O₁₂P
• 分子量: 592.537
• InChiKey: KRCZZAQRKCZSCP-PVBFVMNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4-甲苯硫酚 、 [(3aR,5R,6R,7S,7aR)-6,7-diacetyloxy-2-bis(phenylmethoxy)phosphoryl-2-methyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl acetate 在 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以63%的产率得到p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Glycosyl Phosphites as Glycosylation Reagents: Scope and Mechanism

  摘要：

  The glycosylation reactions with glycosyl phosphites in the presence of catalytic amounts of TMSOTf at low temperature have been studied with different donors and accepters for the synthesis of several glycosides, including O-glycosides, S-glycosides, C-glycosides, and glycopeptides. Mechanistic investigations of the reactions indicate that the glycosyl phosphite is activated by either TfOH or TMSOTf, depending on how the substrates are mixed. When the acceptor is treated with TMSOTf first, the glycosyl phosphite is activated by the resulting TfOH. The glycosyl phosphite can also be activated by TMSOTf directly. The best result is, however, to mix the acceptor and TMSOTf first, followed by addition of the glycosyl phosphite.

  DOI：

  10.1021/jo00083a032
• 作为产物：
  描述：

  Dibenzyl 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl phosphite 在 1,3,5-三甲氧基苯 、 molecular sieve 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到[(3aR,5R,6R,7S,7aR)-6,7-diacetyloxy-2-bis(phenylmethoxy)phosphoryl-2-methyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl acetate
  参考文献：
  名称：

  Glycosyl Phosphites as Glycosylation Reagents: Scope and Mechanism

  摘要：

  The glycosylation reactions with glycosyl phosphites in the presence of catalytic amounts of TMSOTf at low temperature have been studied with different donors and accepters for the synthesis of several glycosides, including O-glycosides, S-glycosides, C-glycosides, and glycopeptides. Mechanistic investigations of the reactions indicate that the glycosyl phosphite is activated by either TfOH or TMSOTf, depending on how the substrates are mixed. When the acceptor is treated with TMSOTf first, the glycosyl phosphite is activated by the resulting TfOH. The glycosyl phosphite can also be activated by TMSOTf directly. The best result is, however, to mix the acceptor and TMSOTf first, followed by addition of the glycosyl phosphite.

  DOI：

  10.1021/jo00083a032