(3R,3aS,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate | 72631-59-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,3aS,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate
• 英文别名: (1S,4R,5R,8R)-8-(p-toluenesulfonyloxy)-2,6-dioxabicyclo[3.3.0]octan-4-ol；[(3R,3aR,6R,6aS)-3-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl] 4-methylbenzenesulfonate
• CAS: 72631-59-5
• 化学式: C₁₃H₁₆O₆S
• 分子量: 300.332
• InChiKey: FGJZRMSVFCYGGE-FDYHWXHSSA-N

物化性质

• 熔点：
  104-105 °C(Solv: ethyl acetate (141-78-6); isopropanol (67-63-0))
• 沸点：
  509.6±50.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  90.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,3aS,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate 在 sodium azide 、 5%-palladium/activated carbon 、 四丁基溴化铵 、 氢气 、 1-butyl-3-methylimidazolium Tetrafluoroborate 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0~120.0 ℃ 、275.01 kPa 条件下， 反应 5.0h， 生成 (3S,3aR,6R,6aS)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-amine
  参考文献：
  名称：

  基于异甘露聚糖的N-保护氨基酸的新型肽模拟物，可作为丙型肝炎病毒NS3丝氨酸蛋白酶的潜在抑制剂

  摘要：

  丙型肝炎病毒（HCV）是最重要的黄病毒之一。它具有丝氨酸蛋白酶，这对于病毒复制很重要，并且该酶构成新的抗逆转录病毒药物的合适靶标。本文中，我们公开了一系列丝氨酸蛋白酶的酰胺和酯肽模拟物抑制剂，它们都是通过异甘露糖衍生物与N-保护的氨基酸的偶联反应而获得的。精氨酸衍生物19在100μM浓度下抑制了NS3 / 4A丝氨酸蛋白酶的45％，分子模型研究表明19与该酶的活性位点相互作用。

  DOI：

  10.2174/157017812800233787
• 作为产物：
  描述：

  甘露醇 在 吡啶 、 盐酸 作用下， 以 水 为溶剂， 反应 84.0h， 生成 (3R,3aS,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Synthesis and structure of 1,4:3,6-dianhydro-2-O-p-tosyl-D-mannitol

  摘要：

  1,4:3,6-Dianhydro-2-O-p-tosyl-D-mannitol (3) has been isolated from the reaction of 1,4:3,6-dianhydro-D-mannitol (2) and p-toluenesulfonyl chloride (1:2 mole ratio) in pyridine in 19% yield after fractional crystallization. It crystallizes in the orthorhombic space group P2(1)2(1)2(1) (Z = 4) With a = 6.064(2), b = 8.347(1) and c = 26.455(16) Angstrom. Disorder associated with the unsubstituted furanose ring provides two arrangements, rings B and C, with two sets of sites for both the hydroxyl group and a ring carbon atom: the relative occupancy of ring B: ring C = 0.53(1):0.47(1). Distinct H-bonding situations (both intra- and inter-molecular) are associated with the two arrangements. The conformations of the unsubstituted furanose ring with the weaker intramolecular II-bonding (ring B) and the tosyl-substituted ring (ring A) are very similar, being 1:2 mixtures of envelope [E-3] and twist forms [T-3(4)]: the stronger H-bonding in ring C results instead in a conformation made up from a 30:70 mixture of E-o and T-4(o) forms. The H-1-NMR spectrum for 3 indicates that the average solution conformation is also a mixture of envelope and twist forms and is similar to that of the A/B solid-state arrangement.

  DOI：

  10.1007/bf02575984

文献信息

• Novel bacterial topoisomerase inhibitors derived from isomannide
  作者：Antony Okumu、Yanran Lu、Sheri Dellos-Nolan、Jonathan L. Papa、Bryan Koci、Nicholas T. Cockroft、Judith Gallucci、Daniel J. Wozniak、Jack C. Yalowich、Mark J. Mitton-Fry

  DOI：10.1016/j.ejmech.2020.112324

  日期：2020.8

  A series of Novel Bacterial Topoisomerase Inhibitors (NBTIs) employing a linker derived from isomannide were synthesized and evaluated. Reduced hERG inhibition was observed compared to structure-matched analogues with different linkers, and compound 6 showed minimal proarrhythmic potential using an in vitro panel of cardiac ion channels. Compound 6 also displayed excellent activity against fluoroquinolone-resistant

  合成和评估了一系列使用衍生自异甘露糖苷的接头的新型细菌拓扑异构酶抑制剂（NBTI）。与具有不同接头的结构匹配类似物相比，观察到了降低的hERG抑制作用，并且使用体外离子通道检测化合物6的心律失常潜力最小。化合物6还显示出对耐氟喹诺酮类MRSA（MIC90 = 2μg/ mL）和其他革兰氏阳性病原体的出色活性。
• [EN] TETRAHYDROFURO [3, 2-B] PYRROL-3-ONE DERIVATIVES AS INHIBITORS OF CYSTEINE PROTEASES<br/>[FR] DÉRIVÉS DE TÉTRAHYDROFURO[3,2-B]PYRROL-3-ONE COMME INHIBITEURS DE CYSTÉINE PROTÉASES
  申请人：AMURA THERAPEUTICS LTD

  公开号：WO2009144450A1

  公开（公告）日：2009-12-03

  A compound of formula (I), or a pharmaceutically acceptable salt, hydrate, complex or pro-drug thereof, wherein one of R1 and R2 is H, and the other is selected fromC1-8-alkyl, C3-6-cycloalkyl and C1-8-alkyl-C5-10-aryl; R3 is selected from tert-butyl, cyclopentyl and 1-methylcyclopentyl; R9 is selected from the following: (F). The invention further relates to pharmaceutical compositions comprising compounds of formula (I), and the use of such compounds in the treatment of various diseases.

  一种具有式（I）的化合物，或其药学上可接受的盐、水合物、络合物或前药，其中R1和R2中的一个是H，另一个选自C1-8-烷基、C3-6-环烷基和C1-8-烷基-C5-10-芳基；R3选自叔丁基、环戊基和1-甲基环戊基；R9选自以下内容：（F）。本发明还涉及包括式（I）化合物的药物组合物，以及利用这些化合物治疗各种疾病。
• Stereospecific method for the preparation of dioxa-bicyclooctane compounds
  申请人：Lacer, S.A.

  公开号：US07635782B1

  公开（公告）日：2009-12-22

  This invention relates to a new method for the stereospecific thiocarboxylation of organic compounds for the preparation of compounds according to formula (I): wherein a compound of formula (II): is reacted with a compound of formula (IIIa) or (IIIb): then treating the obtained product with a thiocarboxylic acid or a salt thereof, and subsequently carrying out a nitration reaction.

  本发明涉及一种用于立体特异性有机化合物的硫代羧化新方法，用于制备符合以下化学式（I）的化合物：其中化学式（II）的化合物与化学式（IIIa)或（IIIb)的化合物发生反应：然后用硫代羧酸或其盐处理所得产物，随后进行硝化反应。
• [EN] BACTERIAL TOPOISOMERASE INHIBITORS DERIVED FROM ISOMANNIDE<br/>[FR] INHIBITEURS BACTÉRIENS DE LA TOPOISOMÉRASE DÉRIVÉS DE L'ISOMANNIDE
  申请人：OHIO STATE INNOVATION FOUNDATION

  公开号：WO2021150954A1

  公开（公告）日：2021-07-29

  Disclosed are bacterial topoisomerase inhibitors employing a linker derived from isomannide. Reduced hERG inhibition was observed compared to structure-matched analogues with different linkers.

  揭示了利用源自异甘露糖的连接剂的细菌拓扑异构酶抑制剂。与使用不同连接剂的结构匹配的类似物相比，观察到了较低的hERG抑制作用。
• Synthesis and Applications of Novel Bis(ammonium) Chiral Ionic Liquids Derived from Isomannide
  作者：Vineet Kumar、Carl E. Olsen、Susan J. C. Schäffer、Virinder S. Parmar、Sanjay V. Malhotra

  DOI：10.1021/ol071390y

  日期：2007.9.1

  Carbohydrate-based novel bis(ammonium) chiral ionic liquids have been synthesized by following a straightforward protocol using isomannide as the substrate. Their applications in chiral discrimination and optical resolution of racemates have been established.

  基于碳水化合物的新型双（铵）手性离子液体已通过遵循简单的方法（使用异甘露醇作为底物）进行合成。已经建立了它们在外消旋物的手性鉴别和光学拆分中的应用。