(2R,3S,4S)-2-(hydroxymethyl)tetrahydrothiophene-3,4-diol | 160882-26-8

• 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: (2R,3S,4S)-2-(hydroxymethyl)tetrahydrothiophene-3,4-diol
• 英文别名: 1,4-dideoxy-1,4-epithio-D-arabinitol；1-deoxy-4-thio-D-arabinofuranose；1,4-anhydro-4-thio-D-arabinitol；1,4-epithio-D-arabinitol；(2R,3S,4S)-2-(hydroxymethyl)thiolane-3,4-diol
• CAS: 160882-26-8
• 化学式: C₅H₁₀O₃S
• 分子量: 150.199
• InChiKey: VLVSFIRYIVAVKW-WDCZJNDASA-N

物化性质

• 沸点：
  327.4±42.0 °C(Predicted)
• 密度：
  1.490±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  9
• 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：
  86
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-2-(hydroxymethyl)tetrahydrothiophene-3,4-diol 在 sodium hydride 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 13.5h， 生成 [(2S,3S)-4-[(2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)thiolan-1-ium-1-yl]-1,3-dihydroxybutan-2-yl] sulfate
  参考文献：
  名称：

  天然存在的糖苷酶抑制剂 Salacinol 的改进合成

  摘要：

  描述了天然存在的锍离子、salacinol 的改进合成。Salacinol 是斯里兰卡和印度传统上用于治疗 2 型糖尿病的五层龙水提取物中的活性成分之一。合成策略至少依赖于 2,3,5-tri-O-benzyl- 或 2,3,5-tri-Op-methoxybenzyl-1,4-anhydro-4-thio-D-arabinitol 的亲核攻击苯亚甲基保护的 L-赤藓糖醇-1,3-环硫酸盐在 1,1,1,3,3,3-六氟-2-丙醇中的受阻碳作为溶剂。将这些反应与苄基保护的 L-赤藓糖醇-1.3-环硫酸盐以及丙酮和 2-丙醇中的反应进行比较。与亚苄基保护的环状硫酸盐的反应获得了极好的产率。

  DOI：

  10.1055/s-2003-40353
• 作为产物：
  描述：

  [(2S,3S)-4-[(2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)thiolan-1-ium-1-yl]-1,3-dihydroxybutan-2-yl] sulfate 在 NaPMe 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以44%的产率得到(2R,3S,4S)-2-(hydroxymethyl)tetrahydrothiophene-3,4-diol
  参考文献：
  名称：

  Absolute Stereostructure of Potent α-Glucosidase Inhibitor, Salacinol, with Unique Thiosugar Sulfonium Sulfate Inner Salt Structure from Salacia reticulata

  摘要：

  A most potent alpha-glucosidase inhibitor named salacinol has been isolated from an antidiabetic Ayurvedic traditional medicine. Salacia reticulata WIGHT, through bioassay-guided separation. The absolute stereostructure of salacinol was determined on the basis of chemical and physicochemical evidence, which included the alkaline degradation of salacinol to 1-deoxy-4-thio-D-arabinofuranose and the X-ray crystallographic analysis, to be the unique spiro-like configuration of the inner salt comprised of 1-deoxy-4-thio-D-arabinofuranosyl sulfonium cation and 1'-deoxy-D-erythrosyl-3'-sulfate anion. Salacinol showed potent inhibitory activities on several alpha-glucosidases, such as maltase, sucrase, and isomaltase, and the inhibitory effects on serum glucose levels in maltose- and sucrose-loaded rats (in vivo) were found to be more potent than that of acarbose, a commercial alpha-glucosidase inhibitor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00422-9

文献信息

• Glycosidase inhibitors and methods of synthesizing same
  申请人：Pinto Mario Brian

  公开号：US20050065139A1

  公开（公告）日：2005-03-24

  A method for synthesizing Salacinol, its stereoisomers, and analogues, homologues and other derivatives thereof potentially useful as glycolsidase inhibitors. The compounds of the invention may have the general formula (I) or (II): The synthetic schemes comprise reacting a cyclic sulfate with a 5-membered ring sugar containing a heteroatom (X). The heteroatom preferably comprises sulfur, selenium, or nitrogen. The cyclic sulfate and ring sugar reagents may be readily prepared from carbohydrate precursors, such as D-glucose, L-glucose, D-xylose and L-xylose. The target compounds are prepared by opening of the cyclic sulfates by nucleophilic attack of the heteroatoms on the 5-membered ring sugars. The resulting heterocyclic compounds have a stable, inner salt structure comprising a heteroatom cation and a sulfate anion. The synthetic schemes yield various stereoisomers of the target compounds in moderate to good yields with limited side-reactions.

  一种合成Salacinol及其立体异构体、类似物、同系物和其他衍生物的方法，可能用作糖苷酶抑制剂。本发明的化合物可能具有一般式(I)或(II)：合成方案包括将环状硫酸酯与含有杂原子(X)的5元环糖反应。杂原子优选包括硫、硒或氮。环状硫酸酯和环糖试剂可以从碳水化合物前体（如D-葡萄糖、L-葡萄糖、D-木糖和L-木糖）中轻松制备。目标化合物是通过杂原子对5元环糖的亲核攻击打开环状硫酸酯来制备的。所得的杂环化合物具有稳定的内盐结构，包括一个杂原子阳离子和一个硫酸酯阴离子。合成方案以中等至良好的产率产生目标化合物的各种立体异构体，副反应有限。
• De novo synthesis of 1-deoxythiosugars
  作者：Thanikachalam Gunasundari、Srinivasan Chandrasekaran

  DOI：10.1016/j.carres.2013.09.009

  日期：2013.12

  biologically potent and novel 1-deoxythiosugars is accomplished. Introduction of sulfur mediated by benzyltriethylammonium tetrathiomolybdate, as a sulfur transfer reagent through nucleophilic double displacement of tosylate in alpha,omega-di-O-tosyl aldonolactones in an intramolecular fashion is the key feature. The subsequent reduction of thiosugar lactones with borohydride exchange resin (BER) offers a

  完成了有效且新颖的具有生物活性的新型1-脱氧硫糖的化学合成。通过硫代甲酸酯以α，ω-二-O-甲苯磺酰基内酯内酯的亲核双取代以分子内方式引入作为硫转移剂的苄基三乙基铵四硫代钼酸铵是主要特征。随后用硼氢化物交换树脂（BER）还原硫糖内酯可提供许多脱氧硫糖，总收率良好。
• Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor. Part 2
  作者：Genzoh Tanabe、Kanjyun Matsuoka、Masahiro Yoshinaga、Weijia Xie、Nozomi Tsutsui、Mumen F. A. Amer、Shinya Nakamura、Isao Nakanishi、Xiaoming Wu、Masayuki Yoshikawa、Osamu Muraoka

  DOI：10.1016/j.bmc.2012.09.006

  日期：2012.11

  To examine the role of the side chain of kotalanol (2), a potent natural α-glucosidase inhibitor isolated from Salacia reticulata, on inhibitory activity, four diastereomers (11a–11d) with reversed configuration (S) at the C-4′ position in the side chain were synthesized and evaluated. Two of the four (11b and 11d) significantly lost their inhibitory activity against both maltase and sucrase, while

  为了检查kotalanol（的侧链的作用2），一种有效的天然α葡萄糖苷酶抑制剂分离自五层龙网状，上抑制活性，四个非对映体（11A - 11D）具有相反构型（小号）在C-4'位合成并评估了侧链中的α。四个中的两个（11b和11d）明显失去了对麦芽糖酶和蔗糖酶的抑制活性，而另外两个（11a和11c））在相当大程度上维持了抑制活性，响应于5'和6'位置上的羟基的立体化学的变化而显示出独特的活性。参考对这些抑制剂与hNtMGAM的计算机对接研究，合理化了不同的活性。针对异麦芽糖酶，所有四个类似物都显示出强大的抑制活性，以及2，并且11b和11d表现出酶选择性。
• Synthesis and Conformational Analysis of Bicyclic Sulfonium Salts. Structures Related to the Glycosidase Inhibitor Australine
  作者：Nag S. Kumar、B. Mario Pinto

  DOI：10.1021/jo051560p

  日期：2006.4.1

  The syntheses of eight sulfonium compounds with structures related to the naturally occurring pyrrolizidine alkaloid, australine, in which the bridgehead nitrogen atom is replaced by a sulfonium ion, are described. The synthetic strategy relies on the intramolecular attack of a cyclic thioether across a terminal double bond in the presence of a suitable electrophile. We postulate that these compounds

  描述了八种sulf化合物的合成，这些化合物具有与天然存在的吡咯并iz烷生物碱，澳新碱有关的结构，其中桥头氮原子被sulf离子取代。合成策略依赖于在合适的亲电试剂存在下环状硫醚通过末端双键的分子内攻击。我们假设这些化合物在硫原子上具有永久的正电荷，将在糖苷酶催化的水解反应中模拟高度不稳定的氧杂碳鎓离子过渡态。基于1 H- 1的分析，这些化合物的构象偏爱H邻位耦合常数和1D-NOESY数据归因于空间和静电相互作用。这些化合物将用于与糖苷酶的构效关系研究。
• COMPOUND USEFUL FOR MANUFACTURING SALACINOL, METHOD FOR MANUFACTURING THE COMPOUND, METHOD FOR MANUFACTURING SALACINOL, METHODS FOR PROTECTING AND DEPROTECTING DIOL GROUP, AND PROTECTIVE AGENT FOR DIOL GROUP
  申请人：FUJIFILM Corporation

  公开号：US20170001974A1

  公开（公告）日：2017-01-05

  An object of the present invention is to provide a novel compound useful for manufacturing salacinol, a method for manufacturing the compound, a method for manufacturing salacinol, methods for protecting and deprotecting a diol group, and a protective agent for a diol group. A compound represented by Formula (1) is a compound useful for manufacturing salacinol. (In the formula, each of R 1a and R 1b is a hydrogen atom or a hydroxy protective group; R 2 is a hydroxy group or the like; and R 3 is a hydroxy group or the like.)

  本发明的一个目的是提供一种用于制造沙拉西诺的新型化合物，一种制造该化合物的方法，一种制造沙拉西诺的方法，保护和去保护二醇基团的方法，以及二醇基团的保护剂。由式（1）表示的化合物是用于制造沙拉西诺的化合物。（在该式中，R1a和R1b中的每一个是氢原子或羟基保护基；R2是羟基或类似物；R3是羟基或类似物。）