(1S,3R,4R,5S,6R,7R)-7-acetoxy-6-benzyloxy-5-benzyloxymethyl-4-benzyloxy-3-acetoxymethyl-2,8-dioxabicyclo[3.2.1]octane | 217325-03-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,3R,4R,5S,6R,7R)-7-acetoxy-6-benzyloxy-5-benzyloxymethyl-4-benzyloxy-3-acetoxymethyl-2,8-dioxabicyclo[3.2.1]octane
• 英文别名: [(1S,3R,4R,5S,6R,7R)-7-acetyloxy-4,6-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-2,8-dioxabicyclo[3.2.1]octan-3-yl]methyl acetate
• CAS: 217325-03-6
• 化学式: C₃₃H₃₆O₉
• 分子量: 576.643
• InChiKey: YUFPUPQSRGMKRV-KVTCHKJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R,5S,6R,7R)-7-acetoxy-6-benzyloxy-5-benzyloxymethyl-4-benzyloxy-3-acetoxymethyl-2,8-dioxabicyclo[3.2.1]octane 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以91%的产率得到(1S,3R,4R,5S,6R,7R)-7-hydroxy-6-benzyloxy-5-benzyloxymethyl-4-benzyloxy-3-hydroxymethyl-2,8-dioxabicyclo[3.2.1]octane
  参考文献：
  名称：

  An approach to the bicyclic core of the zaragozic acids via the aldol reaction between methyl (α-D-xylofuranoside)uronate and D-(R)-glyceraldehyde acetonide

  摘要：

  The aldol reaction between methyl (methyl-3-O-benzyl-2-O-methoxymethyl-alpha-D-xylofurano-side)uronate and D-(R)-glyceraldehyde acetonide, promoted by cerium(III) chloride, led to three diastereoisomers in good yield and high level of stereoselectivity at the newly created quaternary center of the furanoside. Under acidic conditions, the aldol derivatives undergo transketalization to afford different bicyclic ketal isomers. This reaction was used as the key step in the synthesis of a functionalized bicyclic core of the zaragozic acids. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00637-7
• 作为产物：
  描述：

  methyl (methyl-3-O-benzyl-2-O-methoxymethyl-4-C-(hydroxy-(2,2-dimethyl[1,3]dioxolan-4-yl)methyl)-α-D-xylo/β-L-arabinofuranoside) uronate 在 lithium aluminium tetrahydride 、 Dowex 50W 、 sodium hydride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 25.0h， 生成 (1S,3R,4R,5S,6R,7R)-7-acetoxy-6-benzyloxy-5-benzyloxymethyl-4-benzyloxy-3-acetoxymethyl-2,8-dioxabicyclo[3.2.1]octane
  参考文献：
  名称：

  An approach to the bicyclic core of the zaragozic acids via the aldol reaction between methyl (α-D-xylofuranoside)uronate and D-(R)-glyceraldehyde acetonide

  摘要：

  The aldol reaction between methyl (methyl-3-O-benzyl-2-O-methoxymethyl-alpha-D-xylofurano-side)uronate and D-(R)-glyceraldehyde acetonide, promoted by cerium(III) chloride, led to three diastereoisomers in good yield and high level of stereoselectivity at the newly created quaternary center of the furanoside. Under acidic conditions, the aldol derivatives undergo transketalization to afford different bicyclic ketal isomers. This reaction was used as the key step in the synthesis of a functionalized bicyclic core of the zaragozic acids. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00637-7

文献信息

• A short synthesis of the bicyclic core of the zaragozic acids
  作者：Pierre Fraisse、Issam Hanna、Jean-Yves Lallemand

  DOI：10.1016/s0040-4039(98)01726-2

  日期：1998.10

  A synthesis of the highly functionalized bicyclic core of the zaragozic acids is described, in which the key step involves the construction of the C4 quaternary carbon center by a CeCl3-promoted aldol reaction between the α-D-xylofuranuronic acid derivative 2 and D-(R)-glyceraldehyde acetonide.

  描述了zaragozic酸的高度官能化双环核的合成方法，其中关键步骤涉及通过CeCl 3促进的α-D-木呋喃糖醛酸衍生物2和D-之间的CeCl 3促进的醛醇缩合反应构建C4季碳中心。（R）-甘油醛丙酮化物。