5,6-O-isopropylidene-3-O-methyl-1,2-O-(S)-trichloroethylidene-α-D-glucofuranose | 872321-62-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-O-isopropylidene-3-O-methyl-1,2-O-(S)-trichloroethylidene-α-D-glucofuranose
• CAS: 872321-62-5
• 化学式: C₁₂H₁₇Cl₃O₆
• 分子量: 363.622
• InChiKey: KQPMOWTUFUGVOK-PXSBVEPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5,6-O-isopropylidene-3-O-methyl-1,2-O-(S)-trichloroethylidene-α-D-glucofuranose 在 盐酸 、 sodium periodate 、 水 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 为溶剂， 反应 7.0h， 生成 (4R)-5-eno-4,7-epidioxy-3-O-methyl-1,2-O-(S)-trichloroethylidene-5,6,8-trideoxy-α-D-threo-1,4-furano-4,7-diulo-octose
  参考文献：
  名称：

  Stable spiro-endoperoxides by sunlight-mediated photooxygenation of 1,2-O-alkylidene-5(E)-eno-5,6,8-trideoxy-α-d-xylo-oct-1,4-furano-7-uloses

  摘要：

  Sunlight-mediated photooxygenation of 3-O-acetyl and 3-O-methyl derivatives of 1,2-O-alkylidene-5(E)-eno-5,6,8-tride-oxy-alpha-D-xylo-oct-1,4-furano-7-uloses (1 a-e) in carbon tetrachloride solution gave stable 4,7-epidioxy derivatives in 4R (2a-e) and 4S (3a-e) configurations. The presence of an endo alkyl, on the 1,2-O-alkylidene group and its size, resulted in an increase of the yield of the 4S isomers. 3-O-Acetyl derivatives yielded products as a mixture of C-7 anomers, whereas 3-O-methyl derivatives gave pure single stereoisomers. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.09.006
• 作为产物：
  描述：

  β-氯醛糖 在 对甲苯磺酸 、 barium(II) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 5,6-O-isopropylidene-3-O-methyl-1,2-O-(S)-trichloroethylidene-α-D-glucofuranose
  参考文献：
  名称：

  Stable spiro-endoperoxides by sunlight-mediated photooxygenation of 1,2-O-alkylidene-5(E)-eno-5,6,8-trideoxy-α-d-xylo-oct-1,4-furano-7-uloses

  摘要：

  Sunlight-mediated photooxygenation of 3-O-acetyl and 3-O-methyl derivatives of 1,2-O-alkylidene-5(E)-eno-5,6,8-tride-oxy-alpha-D-xylo-oct-1,4-furano-7-uloses (1 a-e) in carbon tetrachloride solution gave stable 4,7-epidioxy derivatives in 4R (2a-e) and 4S (3a-e) configurations. The presence of an endo alkyl, on the 1,2-O-alkylidene group and its size, resulted in an increase of the yield of the 4S isomers. 3-O-Acetyl derivatives yielded products as a mixture of C-7 anomers, whereas 3-O-methyl derivatives gave pure single stereoisomers. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.09.006