1-[(3aR,4S,6R,7S,7aS)-4-((3aR,4S,6R,7S,7aS)-3-Acetyl-6-benzyloxymethyl-2,2-dimethyl-4-phenylsulfanyl-hexahydro-pyrano[3,4-d]oxazol-7-yloxy)-7-benzyloxy-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-pyrano[3,4-d]oxazol-3-yl]-ethanone | 158226-47-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(3aR,4S,6R,7S,7aS)-4-((3aR,4S,6R,7S,7aS)-3-Acetyl-6-benzyloxymethyl-2,2-dimethyl-4-phenylsulfanyl-hexahydro-pyrano[3,4-d]oxazol-7-yloxy)-7-benzyloxy-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-pyrano[3,4-d]oxazol-3-yl]-ethanone
• 英文别名: 1-[(3aR,4S,6R,7S,7aS)-4-[[(3aR,4S,6R,7S,7aS)-3-acetyl-2,2-dimethyl-6-(phenylmethoxymethyl)-4-phenylsulfanyl-4,6,7,7a-tetrahydro-3aH-pyrano[3,4-d][1,3]oxazol-7-yl]oxy]-2,2-dimethyl-7-phenylmethoxy-6-(phenylmethoxymethyl)-4,6,7,7a-tetrahydro-3aH-pyrano[3,4-d][1,3]oxazol-3-yl]ethanone
• CAS: 158226-47-2
• 化学式: C₄₉H₅₈N₂O₁₀S
• 分子量: 867.073
• InChiKey: PMTRDJBMRFKBRK-WISFGODQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  62
• 可旋转键数：
  15
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-[(3aR,4S,6R,7S,7aS)-4-((3aR,4S,6R,7S,7aS)-3-Acetyl-6-benzyloxymethyl-2,2-dimethyl-4-phenylsulfanyl-hexahydro-pyrano[3,4-d]oxazol-7-yloxy)-7-benzyloxy-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-pyrano[3,4-d]oxazol-3-yl]-ethanone 在 palladium on activated charcoal 盐酸 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 1.5h， 生成 demethylallosamidin
  参考文献：
  名称：

  Synthesis of demethylallosamidin, a yeast chitinase inhibitor; use of disaccharide glycosyl donor carrying novel neighboring group

  摘要：

  In the synthesis of novel pseudotrisaccharide called demethylallosamidin, a thioglycoside carrying the 2-acetamido group served as an efficient glycosyl donor through undergoing specific N,O-isopropylidenation at the 2- and 3-positions which prohibits oxazoline ring formation during the glycosidation reaction.

  DOI：

  10.1016/s0040-4039(00)73136-4
• 作为产物：
  描述：

  1-((2R,4aR,6S,6aR,9aS,9bS)-6-(((3aR,4S,6R,7S,7aS)-3-acetyl-2,2-dimethyl-4-(phenylthio)-6-((trityloxy)methyl)hexahydro-4H-pyrano[3,4-d]oxazol-7-yl)oxy)-8,8-dimethyl-2-phenylhexahydro-[1,3]dioxino[4',5':5,6]pyrano[3,4-d]oxazol-7(8H)-yl)ethan-1-one 在 四丁基碘化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 1-[(3aR,4S,6R,7S,7aS)-4-((3aR,4S,6R,7S,7aS)-3-Acetyl-6-benzyloxymethyl-2,2-dimethyl-4-phenylsulfanyl-hexahydro-pyrano[3,4-d]oxazol-7-yloxy)-7-benzyloxy-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-pyrano[3,4-d]oxazol-3-yl]-ethanone
  参考文献：
  名称：

  Synthesis of demethylallosamidin, a yeast chitinase inhibitor; use of disaccharide glycosyl donor carrying novel neighboring group

  摘要：

  In the synthesis of novel pseudotrisaccharide called demethylallosamidin, a thioglycoside carrying the 2-acetamido group served as an efficient glycosyl donor through undergoing specific N,O-isopropylidenation at the 2- and 3-positions which prohibits oxazoline ring formation during the glycosidation reaction.

  DOI：

  10.1016/s0040-4039(00)73136-4

文献信息

• Synthesis of demethylallosamidin, a yeast chitinase inhibitor; use of disaccharide glycosyl donor carrying novel neighboring group
  作者：Shunya Takahashi、Hiroyuki Terayama、Hiroyoshi Kuzuhara

  DOI：10.1016/s0040-4039(00)73136-4

  日期：1994.6

  In the synthesis of novel pseudotrisaccharide called demethylallosamidin, a thioglycoside carrying the 2-acetamido group served as an efficient glycosyl donor through undergoing specific N,O-isopropylidenation at the 2- and 3-positions which prohibits oxazoline ring formation during the glycosidation reaction.