(3S,3aS,6S,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate | 1201908-67-9

• 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: (3S,3aS,6S,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate
• 英文别名: 5-O-(4-toluenesulfonyl)-1,4:3,6-dianhydro-L-iditol；monotosylate-5-isoidide；[(3S,3aR,6S,6aS)-3-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl] 4-methylbenzenesulfonate
• CAS: 1201908-67-9
• 化学式: C₁₃H₁₆O₆S
• 分子量: 300.332
• InChiKey: FGJZRMSVFCYGGE-WUHRBBMRSA-N

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：

  (3S,3aS,6S,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到(3S,3aR,6R,6aS)-6-fluorohexahydrofuro[3,2-b]furan-3-ol
  参考文献：
  名称：

  [EN] MONOFLUORINATED DERIVATIVES OF DIANHYDROHEXITOLS AND PROCESSES FOR MAKING THE SAME
  [FR] DÉRIVÉS MONOFLUORÉS DE DIANHYDROHEXITOLS ET LEURS PROCÉDÉS DE PRÉPARATION

  摘要：

  描述了异山梨醇、异甘醇和异异甘醇的新型单氟类似物，以及制备这些单氟类似物的方法。

  公开号：

  WO2013188005A1
• 作为产物：
  描述：

  对甲苯磺酰氯 、 1,4:3,6-dianhydro-L-iditol 在 吡啶 作用下， 反应 24.0h， 以62%的产率得到(3S,3aS,6S,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Isosorbide-based cholinesterase inhibitors; replacement of 5-ester groups leading to increased stability

  摘要：

  Isosorbide-2-carbamate-5-esters are highly potent and selective butyrylcholinesterase inhibitors with potential utility in the treatment of Alzheimer's Disease (AD). They are stable in human plasma but in mouse plasma they undergo hydrolysis at the 5-ester group potentially attenuating in vivo potency. In this paper we explore the role of the 5-position in modulating potency. The focus of the study was to increase metabolic stability while preserving potency and selectivity. Dicarbamates and 5-keto derivatives were markedly less potent than the ester class. The 2-benzylcarbamate-5-benzyl ether was found to be potent (IC50 52 nM) and stable in the presence of mouse plasma and liver homogenate. The compound produces sustained moderate inhibition of mouse butyrylcholinesterase at 1 mg/kg, IP. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.052

文献信息

• 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。
• New stereospecific method for the preparation of dioxa-bicyclooctane compounds
  申请人：LACER, S.A.

  公开号：EP2149577A1

  公开（公告）日：2010-02-03

  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.

  本发明涉及一种有机化合物立体特异性硫代羧化的新方法，用于制备根据式 (I) 的化合物： 式(II)的化合物： 与式 (IIIa) 或 (IIIb) 的化合物反应： 然后用硫代羧酸或其盐处理得到的产物，再进行硝化反应。
• Copper-Catalyzed vs Thermal Step Growth Polymerization of Starch-Derived α-Azide−ω-Alkyne Dianhydrohexitol Stereoisomers: To Click or Not To Click?
  作者：Céline Besset、Sandra Binauld、Mathias Ibert、Patrick Fuertes、Jean-Pierre Pascault、Etienne Fleury、Julien Bernard、Eric Drockenmuller

  DOI：10.1021/ma9024784

  日期：2010.1.12
• US7635782B1
  申请人：——

  公开号：US7635782B1

  公开（公告）日：2009-12-22
• Isosorbide-based cholinesterase inhibitors; replacement of 5-ester groups leading to increased stability
  作者：Gerald P. Dillon、Joanne M. Gaynor、Denise Khan、Ciaran G. Carolan、Sheila A. Ryder、Juan F. Marquez、Sean Reidy、John F. Gilmer

  DOI：10.1016/j.bmc.2009.12.052

  日期：2010.2

  Isosorbide-2-carbamate-5-esters are highly potent and selective butyrylcholinesterase inhibitors with potential utility in the treatment of Alzheimer's Disease (AD). They are stable in human plasma but in mouse plasma they undergo hydrolysis at the 5-ester group potentially attenuating in vivo potency. In this paper we explore the role of the 5-position in modulating potency. The focus of the study was to increase metabolic stability while preserving potency and selectivity. Dicarbamates and 5-keto derivatives were markedly less potent than the ester class. The 2-benzylcarbamate-5-benzyl ether was found to be potent (IC50 52 nM) and stable in the presence of mouse plasma and liver homogenate. The compound produces sustained moderate inhibition of mouse butyrylcholinesterase at 1 mg/kg, IP. (C) 2009 Elsevier Ltd. All rights reserved.