2,4-O-isopropylidene-L-erythritol | 302579-01-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-O-isopropylidene-L-erythritol
• 英文别名: (4R,5S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-5-ol
• CAS: 302579-01-7
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: ODWXYNAGEJVSQH-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-O-isopropylidene-L-erythritol 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 碳酸氢钠 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 乙腈 为溶剂， 生成 2,4-O-isopropylidene-L-erythritol 1,3-cyclic sulfate
  参考文献：
  名称：

  水杨醇的氮类似物的合成及其α-葡萄糖苷酶的抑制活性。

  摘要：

  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。

  DOI：

  10.1248/cpb.49.1503
• 作为产物：
  描述：

  4,6-O-isopropylidene-L-glucose 在 sodium tetrahydroborate 、 sodium periodate 、 溴甲酚绿 、 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 5.17h， 生成 2,4-O-isopropylidene-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。
• Practical Route to Neokotalanol and Its Natural Analogues: Sulfonium Sugars with Antidiabetic Activities
  作者：Yuhao Huang、Yunlong Gao、Weigang He、Zihao Wang、Wei Li、Aijun Lin、Jinyi Xu、Genzoh Tanabe、Osamu Muraoka、Xiaoming Wu、Weijia Xie

  DOI：10.1002/anie.201900761

  日期：2019.5.6

  time. The key strategy features a coupling reaction between thiol derivatives and a diiodide counterpart. The newly designed thiol coupling partner presents high chemical stability, while the diiodide partner could be easily obtained with increased overall yields compared with conventional routes. The intermolecular nucleophilic substitution reaction followed by a diastereoselective intramolecular cyclization

  首次报道了一种高效，多样化的方法，用于合成最初从S藜属植物中分离的所有四种脱-O-磺化α型α-葡萄糖苷酶抑制剂。关键策略是硫醇衍生物与二碘化物对应物之间的偶联反应。新设计的硫醇偶合剂具有较高的化学稳定性，而与常规方法相比，二碘化物偶合剂可以轻松获得，总收率更高。分子间亲核取代反应，随后进行非对映选择性分子内环化，提供了目标五元sulf盐结构，该结构以α-方向连接至多羟基化的侧链部分。
• 一种构建环状锍鎓糖的方法及其在neosalacinol等天然产物合成中的应用
  申请人：中国药科大学

  公开号：CN110078704A

  公开（公告）日：2019-08-02

  本发明属于化学合成领域，具体涉及涉及五层龙属植物中提取的天然产物neosalaprinol、neosalacinol、neoponkoranol以及neokotalanol的全合成方法。该方法由商业途径购买的S‑缩水甘油，D‑阿拉伯糖和D‑葡萄糖为原料，经多步反应合成从五层龙属植物中提取的天然产物neosalaprinol、neosalacinol、neoponkoranol以及neokotalanol。
• Biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chain on the α-glucosidase inhibitory activity
  作者：Genzoh Tanabe、Kazuya Yoshikai、Takanori Hatanaka、Mizuho Yamamoto、Ying Shao、Toshie Minematsu、Osamu Muraoka、Tao Wang、Hisashi Matsuda、Masayuki Yoshikawa

  DOI：10.1016/j.bmc.2006.10.014

  日期：2007.6.1

  De-O-sulfonated analogs (10a, Y(-)=CH(3)OSO(3) and 10b, Y(-)=Cl) of salacinol, a naturally occurring glycosidase inhibitor, and its diastereomer (12a, Y(-)=CH(3)OSO(3)) with L-thiosugar moiety (1,4-dideoxy-1,4-epithio-L-arabinitol) were prepared. Their inhibitory activities against intestinal maltase and sucrase were examined and compared with those of the parent alpha-glycosidase inhibitor, salacinol

  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。
• 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.