Acetic acid (3aR,3bR,6R,6aR,7aR)-2,2-dimethyl-5-oxo-hexahydro-furo[2',3':3,4]cyclopenta[1,2-d][1,3]dioxol-6-yl ester | 172749-99-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (3aR,3bR,6R,6aR,7aR)-2,2-dimethyl-5-oxo-hexahydro-furo[2',3':3,4]cyclopenta[1,2-d][1,3]dioxol-6-yl ester
• 英文别名: [(1R,2R,6R,8R,9R)-4,4-dimethyl-10-oxo-3,5,11-trioxatricyclo[6.3.0.02,6]undecan-9-yl] acetate
• CAS: 172749-99-4
• 化学式: C₁₂H₁₆O₆
• 分子量: 256.255
• InChiKey: RBNYVDVWZIHQFF-VVULQXIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Acetic acid (3aR,3bR,6R,6aR,7aR)-2,2-dimethyl-5-oxo-hexahydro-furo[2',3':3,4]cyclopenta[1,2-d][1,3]dioxol-6-yl ester 在 sodium tetrahydroborate 、 sodium methylate 作用下， 以 甲醇 为溶剂， 以88%的产率得到(R)-1-((3aS,4R,5S,6aR)-4-Hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl)-ethane-1,2-diol
  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：

  (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 、 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 Acetic acid (3aR,3bR,6R,6aR,7aR)-2,2-dimethyl-5-oxo-hexahydro-furo[2',3':3,4]cyclopenta[1,2-d][1,3]dioxol-6-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