2,4-O-isopropylidene-L-erythritol 1,3-cyclic sulfate | 302579-02-8

• 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-L-erythritol 1,3-cyclic sulfate
• 英文别名: (4aR,8aS)-6,6-dimethyl-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3,2]dioxathiine 2,2-dioxide
• CAS: 302579-02-8
• 化学式: C₇H₁₂O₆S
• 分子量: 224.235
• InChiKey: JVIOIFJWAKSEIL-RITPCOANSA-N

物化性质

• 熔点：
  91-92.5 °C (decomp)
• 沸点：
  333.1±42.0 °C(Predicted)
• 密度：
  1.337±0.06 g/cm3(Predicted)

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-L-erythritol 1,3-cyclic sulfate 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Glycosidase Inhibition by cyclic sulfonium compounds

  摘要：

  Inhibitory activities of various cyclic sulfonium compounds including salacinol against several glycosidases were studied and some compounds showed significant inhibition. The sulfonium ion structure was found to be essential for the inhibitory activity. Specific inhibition of salacinol toward rice alpha -glucosidase was ascribed to the tether arm. (C) 2001 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0960-894x(01)00155-x
• 作为产物：
  描述：

  2,4-O-isopropylidene-L-erythritol 1,3-cyclic sulfite 在 ruthenium trichloride 、 sodium periodate 、 碳酸氢钠 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 生成 2,4-O-isopropylidene-L-erythritol 1,3-cyclic sulfate
  参考文献：
  名称：

  salacinol的de-O-磺化类似物的生物学评估，硫酸根阴离子在侧链上对α-葡萄糖苷酶抑制活性的作用。

  摘要：

  天然存在的糖苷酶抑制剂salacinol的De-O-磺化类似物（10a，Y（-）= CH（3）OSO（3）和10b，Y（-）= Cl）及其非对映异构体（12a，Y（-制备具有L-硫糖基部分（1,4-二脱氧-1,4-表硫基-L-阿拉伯糖醇）的）= CH（3）OSO（3））。检查了它们对肠道麦芽糖酶和蔗糖酶的抑制活性，并与亲本α-糖苷酶抑制剂salacinol（1a）进行了比较。化合物10a和10b对两种酶均显示出与1a相同的有效抑制活性，尽管12a是对蔗糖酶和麦芽糖酶的弱抑制剂。这些结果表明1a的O-磺酸根阴离子部分对于抑制活性不是必需的。

  DOI：

  10.1016/j.bmc.2006.10.014

文献信息

• Synthesis of a Nitrogen Analogue of Salacinol and Its .ALPHA.-Glucosidase Inhibitory Activity.
  作者：Osamu MURAOKA、Shao YING、Kazuya YOSHIKAI、Yoshiharu MATSUURA、Eriko YAMADA、Toshie MINEMATSU、Genzoh TANABE、Hisashi MATSUDA、Masayuki YOSHIKAWA

  DOI：10.1248/cpb.49.1503

  日期：——

  naturally occurring sulfonium ion salacinol (1), a potent alpha-glucosidase inhibitor isolated from the Ayruvedic medicine Salacia reticulata, was synthesized and its inhibitory activity against alpha-glucosidase tested. Substitution of the sulfur atom in 1 with a nitrogen reduced the activity considerably. The solid-state stereostructure of the related compound (5) was determined on the basis of single crystal

  合成了天然sulf离子水杨醇（1）的氮类似物4（一种从Ayruvedic药Salacia reticulata中分离出的有效α-葡萄糖苷酶抑制剂），并测试了其对α-葡萄糖苷酶的抑制活性。用氮取代1中的硫原子会大大降低活性。根据单晶X射线测量确定相关化合物（5）的固态立体结构。
• Role of the thiosugar ring in the inhibitory activity of salacinol, a potent natural α-glucosidase inhibitor
  作者：Katsuki Takashima、Shinya Nakamura、Maiko Nagayama、Shinsuke Marumoto、Fumihiro Ishikawa、Weijia Xie、Isao Nakanishi、Osamu Muraoka、Toshio Morikawa、Genzoh Tanabe

  DOI：10.1039/d3ra08485j

  日期：2024.1.31

  the 5-membered thiosugar ring of 1 played an essential role in the potent activities of sulfonium-type inhibitors. The present findings are interesting and important in understanding the function of salacinol, considering that the observed inhibitory activity trend was contrary to the SAR observed in aza-compounds (23, 24, and 25) in a previous study, which suggested that the cyclic structure did not

  在此，氮杂糖的环裂解 ( 24 ) 和截短 ( 25 ) 类似物 1-脱氧野尻霉素 ( 23 ) 表现出与母体化合物相同的抑制活性 ( K i = 4–10 μM) ( 1 , K i = 14μM）。基于这种构效关系 (SAR)，salacinol ( 1 )（一种有效的含硫代糖环的 α-葡萄糖苷酶抑制剂）的四个环裂解（ 26a-26c和27c ）和三个截短（ 28a-28c ）类似物被合成的。生物测定结果显示，所有合成物均无活性，表明1的5元硫糖环在锍类抑制剂的有效活性中发挥着重要作用。考虑到观察到的抑制活性趋势与先前研究中在氮杂化合物（ 23、24和25 ）中观察到的SAR相反，目前的发现对于理解salacinol的功能是有趣且重要的，这表明环状结构并没有促进它们的强抑制活性。
• 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.
• Syntheses and Evaluation as Glycosidase Inhibitor of 1,5-Dideoxy-1,5-imino-D-glucitol Analogs of Salacinol, a Potent α-Glucosidase Inhibitor Isolated from Ayurvedic Medicine, Salacia reticulata
  作者：Osamu Muraoka、Genzoh Tanabe、Takanori Hatanaka、Toshie Minematsu、Hisashi Matsuda、Masayuki Yoshikawa

  DOI：10.3987/com-08-s(d)61

  日期：——

  N-Alkylated deoxynojirimycin (10) bearing the same alkyl chain as salacinol (1), a potent alpha-glucosidase inhibitor isolated from Ayurvedic traditional medicine, Salacia reticulata, was found to inhibit both rat intestinal maltase and sucrase as strong as 1, while 10 has been reported to be inactive against glucoamylase G2 from Aspergillus niger. Its O-desulfate (12) was also found active against these enzymes, and characteristic sulfate anion moiety of I was found not essential for the alpha-glucosidase inhibitory activity.
• Synthesis of Salacinol-d4 as an Internal Standard for Mass-Spectrometric Quantitation of Salacinol, a Potent α-Glucosidase Inhibitor Found in a Traditional Ayurvedic Medicine “Salacia”
  作者：Genzoh Tanabe、Sanami Teramae、Shinsuke Marumoto、Shuhei Okugawa、Fumihiro Ishikawa、Weija Xie、Toshio Morikawa、Osamu Muraoka、Yousuke Kunikata

  DOI：10.3987/com-18-s(t)21

  日期：——

  Accurate quantitative analysis of trace principles in extracts of biologically active natural medicines relies on the use of reliable internal standards (ISs), which, in the case of liquid chromatography-mass spectrometry (LC-MS) analysis, commonly correspond to isotope-labeled stable analogues of the analytes. Herein, we describe the synthesis of salacinol-1,1,5,5-C-d(4) (7), an isotope-labeled stable analogue of salacinol (1), which, in turn, is a potent alpha-glycosidase inhibitor isolated from Salacia (a traditional Ayurvedic medicine), and show that the isotopic purity of the labeled standard is satisfactory for LC-MS analysis.