2,4-O-isopropylidene-1,3-O-sulfonyl-L-erythritol | 302579-00-6

• 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: 2,4-O-isopropylidene-1,3-O-sulfonyl-L-erythritol
• 英文别名: 2,4-O-isopropylidene-D-erythritol 1,3-cyclic sulfate；(4aS,8aR)-6,6-dimethyl-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3,2]dioxathiine 2,2-dioxide
• CAS: 302579-00-6
• 化学式: C₇H₁₂O₆S
• 分子量: 224.235
• InChiKey: JVIOIFJWAKSEIL-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  四氢噻吩 、 2,4-O-isopropylidene-1,3-O-sulfonyl-L-erythritol 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 以65%的产率得到(4R,5R)-2,2-dimethyl-4-((tetrahydro-1H-thiophen-1-ium-1-yl)methyl)-1,3-dioxan-5-yl sulfate
  参考文献：
  名称：

  Synthesis of salacinol

  摘要：

  Salacinol, a new type of alpha-glucosidase inhibitor discovered from the antidiabetic herb, was synthesized for the first time. Under the strategy that salacinol would be synthesized by the coupling reaction between 1,4-epithio-D-arabinitol and the cyclic sulfate of an erythritol derivative, the model coupling reactions between tetrahydrothiophene and versatile cyclic sulfate derivatives were undertaken. These experiments indicated that the 1,3-diol of the cyclic sulfate should be protected with the isopropylidene group, otherwise, even the benzylidene-protected cyclic sulfate decomposed during the reaction. Thus, the salacinol was synthesized using the cyclic sulfate of 1,3-O-isopypropylidene-D-erythritol. The resulting coupling product was deisopropylidenated to afford salacinol. A diastereomer of salacinol was also synthesized. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01129-1
• 作为产物：
  描述：

  4,6-O-isopropylidene-D-glucopyranose 在 ruthenium trichloride sodium tetrahydroborate 、 sodium periodate 、 氯化亚砜 、 溴甲酚绿 、 碳酸氢钠 、 三乙胺 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 5.84h， 生成 2,4-O-isopropylidene-1,3-O-sulfonyl-L-erythritol
  参考文献：
  名称：

  Synthesis of salacinol

  摘要：

  Salacinol, a new type of alpha-glucosidase inhibitor discovered from the antidiabetic herb, was synthesized for the first time. Under the strategy that salacinol would be synthesized by the coupling reaction between 1,4-epithio-D-arabinitol and the cyclic sulfate of an erythritol derivative, the model coupling reactions between tetrahydrothiophene and versatile cyclic sulfate derivatives were undertaken. These experiments indicated that the 1,3-diol of the cyclic sulfate should be protected with the isopropylidene group, otherwise, even the benzylidene-protected cyclic sulfate decomposed during the reaction. Thus, the salacinol was synthesized using the cyclic sulfate of 1,3-O-isopypropylidene-D-erythritol. The resulting coupling product was deisopropylidenated to afford salacinol. A diastereomer of salacinol was also synthesized. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01129-1

文献信息

• Short synthesis of new salacinol analogues and their evaluation as glycosidase inhibitors
  作者：Estelle Gallienne、Mohammed Benazza、Gilles Demailly、Jean Bolte、Marielle Lemaire

  DOI：10.1016/j.tet.2005.03.015

  日期：2005.5

  Versatile synthesis of some analogues of the naturally-occurring α-glucosidase inhibitor salacinol (1), involving thioanhydro alditol moieties with erythro, d,l-threo, xylo, ribo, d-arabino and d-manno configurations is described. Nucleophilic attack at the least-hindered carbon atom of an l- or d-protected erythritol cyclic sulfate by the thioanhydro alditol sulfur atom yielded the desired zwitterionic

  多功能天然存在的α葡萄糖苷酶抑制剂的Salacinol（的一些类似物的合成1），涉及thioanhydro糖醇部分具有赤式，d，1-苏式，木糖，核糖，D-阿糖和D-甘露配置进行说明。硫代脱水醛糖醇硫原子对1-或d-保护的赤藓糖醇环状硫酸盐的最少受阻碳原子的亲核攻击产生了所需的两性离子化合物。此外，2,4-的环硫酸酯的制备ø -亚苄基- d赤藓糖醇和2,4- ö-异亚丙基-1-赤藓糖醇得到改善。酶抑制试验表明，大多数新化合物是弱的但特异性抑制剂，而六元环类似物（β-葡萄糖苷酶：K i = 16μM）则具有良好的抑制活性。
• Synthesis of salacinol
  作者：Hideya Yuasa、Jun Takada、Hironobu Hashimoto

  DOI：10.1016/s0040-4039(00)01129-1

  日期：2000.8

  Salacinol, a new type of alpha-glucosidase inhibitor discovered from the antidiabetic herb, was synthesized for the first time. Under the strategy that salacinol would be synthesized by the coupling reaction between 1,4-epithio-D-arabinitol and the cyclic sulfate of an erythritol derivative, the model coupling reactions between tetrahydrothiophene and versatile cyclic sulfate derivatives were undertaken. These experiments indicated that the 1,3-diol of the cyclic sulfate should be protected with the isopropylidene group, otherwise, even the benzylidene-protected cyclic sulfate decomposed during the reaction. Thus, the salacinol was synthesized using the cyclic sulfate of 1,3-O-isopypropylidene-D-erythritol. The resulting coupling product was deisopropylidenated to afford salacinol. A diastereomer of salacinol was also synthesized. (C) 2000 Elsevier Science Ltd. All rights reserved.