(3S,4S)-tetrahydrothiophene-3,4-diol | 1006383-30-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: (3S,4S)-tetrahydrothiophene-3,4-diol
• 英文别名: trans-Tetrahydrothiophen-3,4-diol；trans-3,4-Dihydroxy-tetrahydro-thiophen；trans-3,4-Dihydroxythiolane；(3S,4S)-thiolane-3,4-diol
• CAS: 1006383-30-7
• 化学式: C₄H₈O₂S
• 分子量: 120.172
• InChiKey: WONPWMKTZAPWSP-QWWZWVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  65.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S)-tetrahydrothiophene-3,4-diol 、 alkaline earth salt of/the/ methylsulfuric acid 生成 2,3-di-O-acetyl-1,4-dideoxy-1,4-thio-D,L-threitol
  参考文献：
  名称：

  Heterocyclisation of free or partially protected alditols via their bis-cyclic sulfate derivatives. Versatile synthesis of aza and thiodeoxyanhydroalditol with erythro, threo, arabino, gulo, talo or manno configuration

  摘要：

  The bis-cyclic sulfate derivatives of erythritol (1), D,L-threitol (5), 3,4-di-O-benzyl-D-mannitol (9), 1,2-O-isopropylidene-D-mannitol (14) and 1-O-benzyl-D,L-xylitol (18) were submitted to nucleophilic attack by allylamine or sodium sulfide. In both cases, heterocyclisation occurred and aza or thioanhydrodeoxyalditols were obtained in moderate to good yields (40 to 89%). With compound 9, 1,5-anhydro-5-thio-L-gulitol (12) was obtained as the main product, a result that is in contrast with previous results reported in the literature using bis-epoxide as bielectrophile intermediate.(1) (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)00791-7
• 作为产物：
  描述：

  1,4-二氯丁烷-2S-3S-二醇 在 sodiumsulfide nonahydrate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以71%的产率得到(3S,4S)-tetrahydrothiophene-3,4-diol
  参考文献：
  名称：

  氢键辅助增强手性亲核催化剂对d，l-1,2-二元醇动力学拆分的反应速率和选择性

  摘要：

  在仅0.5 mol％的联萘基手性N，N -4-二甲基氨基吡啶存在下，开发了一种极有效的d，l - 1,2-二醇的酰基动力学拆分方法（选择性因子高达180）。几个关键实验表明，催化剂的叔醇单元与底物的1,2-二醇单元之间的氢键键合对于加快单酰化速率和实现高对映选择性至关重要。该催化体系可广泛应用于涉及外消旋无环和环状1,2-二醇且具有高选择性因子的底物。d，l-氢安息香和反式的动力学拆分数克级（10 g）的1,2-环己二醇也具有较高的选择性并在中等反应条件下进行：（i）催化剂负载量极低（0.1 mol％）; （ii）容易达到的低反应温度（0°C）；（iii）高底物浓度（1.0 M）；（iv）反应时间短（30分钟）。

  DOI：

  10.1002/adsc.201700057

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。
• [EN] ANTIBACTERIAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIBACTÉRIENS
  申请人：[en]BLACKSMITH MEDICINES, INC.

  公开号：WO2024036170A1

  公开（公告）日：2024-02-15

  Provided herein are heterocyclic compounds and pharmaceutical compositions comprising said compounds that are useful for inhibiting the growth of gram-negative bacteria. The subject compounds and compositions are useful for the treatment of bacterial infections, such as pneumonia.
• Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of <i>d,l</i> -1,2-Diols with Chiral Nucleophilic Catalysts
  作者：Kazuki Fujii、Koichi Mitsudo、Hiroki Mandai、Seiji Suga

  DOI：10.1002/adsc.201700057

  日期：2017.8.17

  An extremely efficient acylative kinetic resolution of d,l‐1,2‐diols in the presence of only 0.5 mol% of binaphthyl‐based chiral N,N‐4‐dimethylaminopyridine was developed (selectivity factor of up to 180). Several key experiments revealed that hydrogen bonding between the tert‐alcohol unit(s) of the catalyst and the 1,2‐diol unit of the substrate is critical for accelerating the rate of monoacylation

  在仅0.5 mol％的联萘基手性N，N -4-二甲基氨基吡啶存在下，开发了一种极有效的d，l - 1,2-二醇的酰基动力学拆分方法（选择性因子高达180）。几个关键实验表明，催化剂的叔醇单元与底物的1,2-二醇单元之间的氢键键合对于加快单酰化速率和实现高对映选择性至关重要。该催化体系可广泛应用于涉及外消旋无环和环状1,2-二醇且具有高选择性因子的底物。d，l-氢安息香和反式的动力学拆分数克级（10 g）的1,2-环己二醇也具有较高的选择性并在中等反应条件下进行：（i）催化剂负载量极低（0.1 mol％）; （ii）容易达到的低反应温度（0°C）；（iii）高底物浓度（1.0 M）；（iv）反应时间短（30分钟）。
• Heterocyclisation of free or partially protected alditols via their bis-cyclic sulfate derivatives. Versatile synthesis of aza and thiodeoxyanhydroalditol with erythro, threo, arabino, gulo, talo or manno configuration
  作者：Virginie Glaçon、Mohammed Benazza、Daniel Beaupère、Gilles Demailly

  DOI：10.1016/s0040-4039(00)00791-7

  日期：2000.6

  The bis-cyclic sulfate derivatives of erythritol (1), D,L-threitol (5), 3,4-di-O-benzyl-D-mannitol (9), 1,2-O-isopropylidene-D-mannitol (14) and 1-O-benzyl-D,L-xylitol (18) were submitted to nucleophilic attack by allylamine or sodium sulfide. In both cases, heterocyclisation occurred and aza or thioanhydrodeoxyalditols were obtained in moderate to good yields (40 to 89%). With compound 9, 1,5-anhydro-5-thio-L-gulitol (12) was obtained as the main product, a result that is in contrast with previous results reported in the literature using bis-epoxide as bielectrophile intermediate.(1) (C) 2000 Published by Elsevier Science Ltd.