5-(E)-eno-3-O-methyl-1,2-O-(S)-trichloroethylidene-5,6,8-trideoxy-α-D-xylo-1,4-furano-7-ulose | 872321-65-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(E)-eno-3-O-methyl-1,2-O-(S)-trichloroethylidene-5,6,8-trideoxy-α-D-xylo-1,4-furano-7-ulose
• 英文别名: (E)-4-[(2S,3aR,5R,6S,6aR)-6-methoxy-2-(trichloromethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]but-3-en-2-one
• CAS: 872321-65-8
• 化学式: C₁₁H₁₃Cl₃O₅
• 分子量: 331.58
• InChiKey: ODSQCKMXLRMRIC-SICHLUOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(E)-eno-3-O-methyl-1,2-O-(S)-trichloroethylidene-5,6,8-trideoxy-α-D-xylo-1,4-furano-7-ulose 以 四氯化碳 为溶剂， 以69%的产率得到(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：

  5,6-O-isopropylidene-1,2-O-trichloroethylidene-α-D-glucofuranose 在 盐酸 、 sodium periodate 、 水 、 barium(II) oxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 5-(E)-eno-3-O-methyl-1,2-O-(S)-trichloroethylidene-5,6,8-trideoxy-α-D-xylo-1,4-furano-7-ulose
  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

文献信息

• 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
  作者：Fatma Çetin、Nilgün Yenil、Levent Yüceer

  DOI：10.1016/j.carres.2005.09.006

  日期：2005.12

  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.