methyl (E)-3-[4-[[(3aR,4S,6R,7S,7aR)-2,2,4-trimethyl-7-sulfooxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-3-[(4-methoxyphenyl)methoxy]phenyl]prop-2-enoate | 868672-03-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (E)-3-[4-[[(3aR,4S,6R,7S,7aR)-2,2,4-trimethyl-7-sulfooxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-3-[(4-methoxyphenyl)methoxy]phenyl]prop-2-enoate
• CAS: 868672-03-1
• 化学式: C₂₇H₃₂O₁₂S
• 分子量: 580.61
• InChiKey: JYGLOOSVEHNJQZ-PJHROWLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  154
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-[4-[[(3aR,4S,6R,7S,7aR)-2,2,4-trimethyl-7-sulfooxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-3-[(4-methoxyphenyl)methoxy]phenyl]prop-2-enoate 在 lithium hydroxide 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.83h， 生成 2-{(E)-3-[3-(4-Methoxy-benzyloxy)-4-((3aR,4S,6R,7S,7aR)-2,2,4-trimethyl-7-sulfooxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-phenyl]-acryloylamino}-ethanesulfonic acid
  参考文献：
  名称：

  Synthesis of the Saccharomicin Fucose−Aglycon Conjugate and Determination of Absolute Configuration

  摘要：

  Schmidt glycosylation of the appropriately protected 3,4-dihydroxycinnamate methyl ester with 2,3,4-triacetoxyfucopyranosyltrichloroacetimidate gives aryl glycoside in high yield and diastereoselectivity. 2-Sulfation of fucose, installation of taurine, and global deprotection of the remaining protecting groups affords the fucose-aglycon conjugate of saccharomicin. This synthesis which arises from L-fucose also establishes the absolute configuration of the reducing terminus of the saccharomicin oligosaccharide.

  DOI：

  10.1021/ol051971s
• 作为产物：
  描述：

  4-hydroxy-3-(4-methoxyphenylmethoxy)benzaldehyde 在 吡啶 、 pyridine-SO3 complex 、 4 A molecular sieve 、 三氟化硼乙醚 、 4-甲基苯磺酸吡啶 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 24.5h， 生成 methyl (E)-3-[4-[[(3aR,4S,6R,7S,7aR)-2,2,4-trimethyl-7-sulfooxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-3-[(4-methoxyphenyl)methoxy]phenyl]prop-2-enoate
  参考文献：
  名称：

  Synthesis of the Saccharomicin Fucose−Aglycon Conjugate and Determination of Absolute Configuration

  摘要：

  Schmidt glycosylation of the appropriately protected 3,4-dihydroxycinnamate methyl ester with 2,3,4-triacetoxyfucopyranosyltrichloroacetimidate gives aryl glycoside in high yield and diastereoselectivity. 2-Sulfation of fucose, installation of taurine, and global deprotection of the remaining protecting groups affords the fucose-aglycon conjugate of saccharomicin. This synthesis which arises from L-fucose also establishes the absolute configuration of the reducing terminus of the saccharomicin oligosaccharide.

  DOI：

  10.1021/ol051971s

文献信息

• Synthesis of the Saccharomicin Fucose−Aglycon Conjugate and Determination of Absolute Configuration
  作者：Joseph M. Pletcher、Frank E. McDonald

  DOI：10.1021/ol051971s

  日期：2005.10.1

  Schmidt glycosylation of the appropriately protected 3,4-dihydroxycinnamate methyl ester with 2,3,4-triacetoxyfucopyranosyltrichloroacetimidate gives aryl glycoside in high yield and diastereoselectivity. 2-Sulfation of fucose, installation of taurine, and global deprotection of the remaining protecting groups affords the fucose-aglycon conjugate of saccharomicin. This synthesis which arises from L-fucose also establishes the absolute configuration of the reducing terminus of the saccharomicin oligosaccharide.