methyl (5R)-2-O-benzyl-6,7-dideoxy-3,4-O-isopropylidene-5-C-methoxy-α-L-arabino-heptopyranoside | 1241386-22-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: methyl (5R)-2-O-benzyl-6,7-dideoxy-3,4-O-isopropylidene-5-C-methoxy-α-L-arabino-heptopyranoside
• 英文别名: (3aR,4R,6R,7R,7aR)-4-ethyl-4,6-dimethoxy-2,2-dimethyl-7-phenylmethoxy-3a,6,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran
• CAS: 1241386-22-0
• 化学式: C₁₉H₂₈O₆
• 分子量: 352.428
• InChiKey: PKBQWDJLIBZNGD-VYIWNADRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲醇 、 (3a'R,6'R,7'R,7a'S)-7'-benzyloxy-6'-methoxy-2',2'-dimethyltetrahydrospiro[cyclopropane-1,4'-[1,3]dioxolo[4,5-c]pyran] 在 mercury(II) trifluoroacetate 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 methyl (5R)-2-O-benzyl-6,7-dideoxy-3,4-O-isopropylidene-5-C-methoxy-α-L-arabino-heptopyranoside 、 methyl (5S)-2-O-benzyl-6,7-dideoxy-3,4-O-isopropylidene-5-C-methoxy-α-L-arabino-heptopyranoside
  参考文献：
  名称：

  Towards the synthesis of new dideoxy δ-dicarbonyl heptoses

  摘要：

  The preparation of a delta-dicarbonyl sugar thorough ring-opening, by a methoxymercuration-demercuration procedure, of a 5-spirocyclopropanated D-galactose derivative, is reported. This method constitutes a new route for the transformation of a hexose into new and interesting delta-dicarbonyl sugars, synthetic precursors of cyclitols, carba- and azasugars. Moreover this is, to our best knowledge, the first reported example of an elongation to a higher sugar starting from a spirocyclopropanated saccharide. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.03.013

文献信息

• Towards the synthesis of new dideoxy δ-dicarbonyl heptoses
  作者：Venerando Pistarà、Maria Assunta Chiacchio、Antonino Corsaro

  DOI：10.1016/j.carres.2010.03.013

  日期：2010.7

  The preparation of a delta-dicarbonyl sugar thorough ring-opening, by a methoxymercuration-demercuration procedure, of a 5-spirocyclopropanated D-galactose derivative, is reported. This method constitutes a new route for the transformation of a hexose into new and interesting delta-dicarbonyl sugars, synthetic precursors of cyclitols, carba- and azasugars. Moreover this is, to our best knowledge, the first reported example of an elongation to a higher sugar starting from a spirocyclopropanated saccharide. (c) 2010 Elsevier Ltd. All rights reserved.