2,3-O-isopropylidene-aldehydo-D-xylose dimethyl acetal | 73707-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-O-isopropylidene-aldehydo-D-xylose dimethyl acetal
• 英文别名: (1R)-1-[(4S,5R)-5-(dimethoxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol
• CAS: 73707-72-9
• 化学式: C₁₀H₂₀O₆
• 分子量: 236.265
• InChiKey: KGJPBAGMRXLQRL-GJMOJQLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-O-isopropylidene-aldehydo-D-xylose dimethyl acetal 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.0h， 生成 (R)-4-((4R,5R)-5-Dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-[1,3,2]dioxathiolane 2,2-dioxide
  参考文献：
  名称：

  Applications of Cyclic Sulfates of vic-Diols:  Synthesis of Episulfides, Olefins, and Thio Sugars

  摘要：

  A new efficient and expeditious one-pot synthesis of thiiranes and olefins from cyclic sulfates of vic-diols is described. Opening of cyclic sulfates with potassium thioacetate or potassium thiocyanate followed by treatment with sodium methoxide led to episulfides. Olefins were obtained when potassium selenocyanate was used as nucleophile, and the obtained monoesters were treated with sodium borohydride. This method was applied to acyclic polyols derived from chiral glycerine, 1,2-isopropylidenehexofuranoses with different subtituents at C-3, and dimethyl acetals derived from pentoses and hexoses. The methodology is highly versatile, and its applicability has been demonstrated by the synthesis of different 4- and 5-thiosugars by opening of the thiirane ring with sodium acetate or lithium aluminum hydride. Reduction with lithium aluminum hydride of the thiocyanate sulfate potassium salt obtained by the opening of cyclic sulfate with KSCN allowed the direct synthesis of 5-deoxy-4-thio- and 6-deoxy-5-thiosugars. Cyclic thiosugars with the sulfur atom in the ring are obtained by acidic hydrolysis of the 5-thiol derivatives of 1,2-O-isopropylidenehexofuranoses and 4-thiopentose dimethyl acetals. Using this method, an efficient synthesis of 5-thio-L-fucose as well as the synthesis of 2,5-dideoxy-4-thiofuranose is described.

  DOI：

  10.1021/jo962066b
• 作为产物：
  描述：

  D-吡喃木糖 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 生成 1,2-O-异亚丙基-alpha-D-呋喃木糖 、 2,3-O-isopropylidene-aldehydo-D-xylose dimethyl acetal
  参考文献：
  名称：

  2-（酰基氨基）-2-脱氧-3,4：5,6-二-O-异亚丙基-醛-d-葡萄糖二甲基和二苄基缩醛的简单制备

  摘要：

  摘要在对甲苯磺酸，2-乙酰胺基-2-脱氧-d-葡萄糖和2-（-）存在下，在1,4-二恶烷溶液中用大量过量的2,2-二甲氧基丙烷或2,2-二苄氧基丙烷处理苄氧基羰基氨基）-2-脱氧-d-葡萄糖以良好的产率得到相应的3,4：5,6-二-O-异亚丙基-乙醛-d-葡萄糖二甲基或二苄基乙缩醛。

  DOI：

  10.1016/s0008-6215(00)83838-0