(1S,4R,5S,6R,7R,8R)-8-hydroxy-7-benzyloxy-6-benzyloxymethyl-5-benzyloxy-4-hydroxy-2,9-dioxabicyclo[4.2.1]nonane

• 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,4R,5S,6R,7R,8R)-8-hydroxy-7-benzyloxy-6-benzyloxymethyl-5-benzyloxy-4-hydroxy-2,9-dioxabicyclo[4.2.1]nonane
• 英文别名: (1R,4R,5S,6R,7R,8R)-5,7-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2,9-dioxabicyclo[4.2.1]nonane-4,8-diol
• 化学式: C₂₉H₃₂O₇
• 分子量: 492.569
• InChiKey: SRGKOUYLOKUKEC-ULFZGVROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (6R)-methyl-3-O-benzyl-2-O-methoxymethyl-4-C-hydroxymethyl-6,7-O-isopropyl-α-D-galacto/α-D-gluco/β-L-altrofuranoside 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 (1S,4R,5S,6R,7R,8R)-8-hydroxy-7-benzyloxy-6-benzyloxymethyl-5-benzyloxy-4-hydroxy-2,9-dioxabicyclo[4.2.1]nonane
  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

• 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
  作者：Pierre Fraisse、Issam Hanna、Jean-Yves Lallemand、Thierry Prangé、Louis Ricard

  DOI：10.1016/s0040-4020(99)00637-7

  日期：1999.10

  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.