(1R,2R,3R,4S)-4-((R)-1,2-Dihydroxy-ethyl)-cyclopentane-1,2,3-triol | 203173-15-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,3R,4S)-4-((R)-1,2-Dihydroxy-ethyl)-cyclopentane-1,2,3-triol
• 英文别名: (1R,2R,3R,4S)-4-[(1R)-1,2-dihydroxyethyl]cyclopentane-1,2,3-triol
• CAS: 203173-15-3
• 化学式: C₇H₁₄O₅
• 分子量: 178.185
• InChiKey: VUTAIQVDIPGRFK-PJEQPVAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  101
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (1R,2R,3R,4S)-4-((R)-1,2-Dihydroxy-ethyl)-cyclopentane-1,2,3-triol 在 高氯酸 作用下， 反应 3.0h， 以84%的产率得到Acetic acid (1R,2R,3R,5S)-2,3-diacetoxy-5-((R)-1,2-diacetoxy-ethyl)-cyclopentyl 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：

  (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 、 盐酸 、 sodium tetrahydroborate 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 20.0h， 生成 (1R,2R,3R,4S)-4-((R)-1,2-Dihydroxy-ethyl)-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