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 | 172750-02-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: [(2S)-2-[(4S,5S)-5-(bromomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-oxo-2H-furan-4-yl] acetate
• CAS: 172750-02-6
• 化学式: C₁₂H₁₅BrO₆
• 分子量: 335.151
• InChiKey: PJKXVIBSQWWCJH-SFGNSQDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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 (S)-5-((4S,5S)-5-bromomethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-oxo-2,5-dihydro-furan-3-yl ester 在 盐酸 、 sodium tetrahydroborate 、 sodium periodate 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 34.0h， 生成 (1R,2R,3S,4R)-4-(hydroxymethyl)cyclopentane-1,2,3-triol
  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 、 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