tert-Butyl-((R)-2,2-dioxo-2λ6-[1,3,2]dioxathian-4-ylmethoxy)-dimethyl-silane | 874620-23-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: tert-Butyl-((R)-2,2-dioxo-2λ6-[1,3,2]dioxathian-4-ylmethoxy)-dimethyl-silane
• CAS: 874620-23-2
• 化学式: C₁₀H₂₂O₅SSi
• 分子量: 282.433
• InChiKey: ZAFXQMRAGPCGQJ-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-Butyl-((R)-2,2-dioxo-2λ6-[1,3,2]dioxathian-4-ylmethoxy)-dimethyl-silane 、 (2R,3S,4S)-2-(hydroxymethyl)tetrahydrothiophene-3,4-diol 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 以20%的产率得到
  参考文献：
  名称：

  Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the α-glucosidase inhibitory activity

  摘要：

  Three analogs (5, 6, and 7) lacking polar substituents in the side chain of a naturally occurring a-glucosidase inhibitor, salacinol (la), were synthesized by the coupling reaction of a thiosugar, 1,4-dideoxy-1,4-epithio-D-arabinitol (3), with cyclic sulfates (8, 9, and 10), and their a-glucosidase inhibitory activities were examined. All these simpler analogs (5, 6, and 7) showed less inhibitory activity compared to la, and proved the importance of cooperative role of the polar substituents for the a-glucosidase inhibitory activity. A practical synthetic route to 3 starting from D-xylose is also described. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.040
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 palladium on activated charcoal 咪唑 、 ruthenium trichloride 、 sodium hydroxide 、 sodium periodate 、 氯化亚砜 、 偶氮二异丁腈 、 氢气 、 次磷酸 、 碳酸氢钠 、 三乙胺 作用下， 以 四氯化碳 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.09h， 生成 tert-Butyl-((R)-2,2-dioxo-2λ6-[1,3,2]dioxathian-4-ylmethoxy)-dimethyl-silane
  参考文献：
  名称：

  Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the α-glucosidase inhibitory activity

  摘要：

  Three analogs (5, 6, and 7) lacking polar substituents in the side chain of a naturally occurring a-glucosidase inhibitor, salacinol (la), were synthesized by the coupling reaction of a thiosugar, 1,4-dideoxy-1,4-epithio-D-arabinitol (3), with cyclic sulfates (8, 9, and 10), and their a-glucosidase inhibitory activities were examined. All these simpler analogs (5, 6, and 7) showed less inhibitory activity compared to la, and proved the importance of cooperative role of the polar substituents for the a-glucosidase inhibitory activity. A practical synthetic route to 3 starting from D-xylose is also described. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.040