(3R,4R,5R)-5-((4S,5S)-5-Bromomethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-dihydro-furan-2-one | 203173-01-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4R,5R)-5-((4S,5S)-5-Bromomethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-dihydro-furan-2-one
• 英文别名: (3R,4R,5R)-5-[(4S,5S)-5-(bromomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxyoxolan-2-one
• CAS: 203173-01-7
• 化学式: C₁₀H₁₅BrO₆
• 分子量: 311.13
• InChiKey: GMUUSEUVBOLCIZ-FMDGEEDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R)-5-((4S,5S)-5-Bromomethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-dihydro-furan-2-one 在 吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 Acetic acid (S)-5-((4S,5S)-5-bromomethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-oxo-2,5-dihydro-furan-3-yl ester
  参考文献：
  名称：

  Highly Functionalized Cyclopentanes by Radical Cyclization of Unsaturated Bromolactones. 2. A Facile Synthesis of the First Carbaaldohexofuranoses and Their Conversion to Carbapentofuranoses

  摘要：

  A novel type of carbasugars, carbaaldohexofuranoses, has been prepared using a 5-exo-trig radical cyclization of C-2 substituted 2,3-unsaturated 7-bromoheptono-1,4-lactones as the key step. During the cyclization step, two-stereogenic centers were farmed with high stereoselectivity. The lactone moieties of the cyclopentane derivatives were reduced to the alcohols, and the following carbahexofuranoses were synthesized: carba-beta-D-mannofuranose, carba-alpha-L-glucofuranose and 5-amino-5-deoxycarba-alpha-L-glucofuranose. Side chain degradation of the two former compounds gave the carbapentofuranoses: carba-alpha-L-xylofuranose and carba-beta-D-lyxofuranose.

  DOI：

  10.1021/jo971928l
• 作为产物：
  描述：

  丙酮 、 (3R,4R,5R)-5-((1R,2S)-3-Bromo-1,2-dihydroxy-propyl)-3,4-dihydroxy-dihydro-furan-2-one 在 camphor-10-sulfonic acid 作用下， 反应 24.0h， 以86%的产率得到(3R,4R,5R)-5-((4S,5S)-5-Bromomethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-dihydro-furan-2-one
  参考文献：
  名称：

  Highly Functionalized Cyclopentanes by Radical Cyclization of Unsaturated Bromolactones. 2. A Facile Synthesis of the First Carbaaldohexofuranoses and Their Conversion to Carbapentofuranoses

  摘要：

  A novel type of carbasugars, carbaaldohexofuranoses, has been prepared using a 5-exo-trig radical cyclization of C-2 substituted 2,3-unsaturated 7-bromoheptono-1,4-lactones as the key step. During the cyclization step, two-stereogenic centers were farmed with high stereoselectivity. The lactone moieties of the cyclopentane derivatives were reduced to the alcohols, and the following carbahexofuranoses were synthesized: carba-beta-D-mannofuranose, carba-alpha-L-glucofuranose and 5-amino-5-deoxycarba-alpha-L-glucofuranose. Side chain degradation of the two former compounds gave the carbapentofuranoses: carba-alpha-L-xylofuranose and carba-beta-D-lyxofuranose.

  DOI：

  10.1021/jo971928l

文献信息

• Highly Functionalized Cyclopentanes by Radical Cyclization of Unsaturated Bromolactones. 2. A Facile Synthesis of the First Carbaaldohexofuranoses and Their Conversion to Carbapentofuranoses
  作者：Anne Marie Horneman、Inge Lundt

  DOI：10.1021/jo971928l

  日期：1998.3.1

  A novel type of carbasugars, carbaaldohexofuranoses, has been prepared using a 5-exo-trig radical cyclization of C-2 substituted 2,3-unsaturated 7-bromoheptono-1,4-lactones as the key step. During the cyclization step, two-stereogenic centers were farmed with high stereoselectivity. The lactone moieties of the cyclopentane derivatives were reduced to the alcohols, and the following carbahexofuranoses were synthesized: carba-beta-D-mannofuranose, carba-alpha-L-glucofuranose and 5-amino-5-deoxycarba-alpha-L-glucofuranose. Side chain degradation of the two former compounds gave the carbapentofuranoses: carba-alpha-L-xylofuranose and carba-beta-D-lyxofuranose.