(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] | 1063665-35-9

• 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: (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]
• 英文别名: (3aR,6R,7R,7aS)-6-methoxy-2,2-dimethyl-7-phenylmethoxyspiro[3a,6,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4,1'-cyclopropane]
• CAS: 1063665-35-9
• 化学式: C₁₈H₂₄O₅
• 分子量: 320.386
• InChiKey: KNLNQMYBPKREOF-KLHDSHLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  methyl 2-O-benzyl-3,4-di-O-isopropylidene-6-deoxy-β-L-arabino-hex-5-enopyranoside 、 二碘甲烷 在 diethylzinc 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 2.0h， 以98%的产率得到(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]
  参考文献：
  名称：

  5-亚甲基半吡喃糖苷通过二卤代，乙氧基羰基和未取代的羧化物进行环丙烷化

  摘要：

  通过亚甲基-锌-碘化物络合物，二氯卡宾和乙氧基羰基铑络合物的加成，使6-脱氧己基-5-enopyranosides的环丙烷化反应提供相应螺环丙烷的最佳收率。令人惊讶地，获得了在4-羟基取代基的上表面具有两个卤素的立体有规螺环丙烷衍生物。为了更深入地了解二氯卡宾环丙烷化工艺，进行了基于DFT定量力学计算的计算研究。

  DOI：

  10.1016/j.tet.2008.07.013

文献信息

• Cyclopropanation of 5-methylene galactopyranosides by dihalo-, ethoxycarbonyl-, and unsubstituted carbenes
  作者：Antonino Corsaro、Maria Assunta Chiacchio、Venerando Pistarà、Antonio Rescifina、Elisa Vittorino

  DOI：10.1016/j.tet.2008.07.013

  日期：2008.9

  6-deoxyhex-5-enopyranosides by methylene-zinc-iodide complex, dichlorocarbene, and rhodium ethoxycarbonyl complex addition afford optimum yields of the corresponding spirocyclopropanes. Surprisingly, a stereospecific spirocyclopropane derivative with the two halogens on the upper face of the 4-hydroxy substituent is obtained. To get more insight on the dichlorocarbene cyclopropanation process a computational study

  通过亚甲基-锌-碘化物络合物，二氯卡宾和乙氧基羰基铑络合物的加成，使6-脱氧己基-5-enopyranosides的环丙烷化反应提供相应螺环丙烷的最佳收率。令人惊讶地，获得了在4-羟基取代基的上表面具有两个卤素的立体有规螺环丙烷衍生物。为了更深入地了解二氯卡宾环丙烷化工艺，进行了基于DFT定量力学计算的计算研究。
• 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.