(2R) 1-<(t-butyldiphenylsilyl)oxy>-2-furanylethanol | 124067-17-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R) 1-<(t-butyldiphenylsilyl)oxy>-2-furanylethanol
• 英文别名: (1R)-2-O-(tert-butyldiphenylsilyl)-1-(2-furanyl)-1,2-ethanediol；1-<(tert-Butyldiphenylsilyl)oxy>-2-furanylethanol；(R)-2-(tert-butyldiphenylsilyloxy)-1-(2-furyl)ethanol；2-(tert-Butyldiphenylsilyloxy)-1-(2-furyl)ethanol；(R)-2-(tert-butyldiphenylsilyloxy)-1-(2-furyl)-1-ethanol；(1R)-2-[tert-butyl(diphenyl)silyl]oxy-1-(furan-2-yl)ethanol
• CAS: 124067-17-0
• 化学式: C₂₂H₂₆O₃Si
• 分子量: 366.532
• InChiKey: HMAIBIQQGSRNMO-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  42.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R) 1-<(t-butyldiphenylsilyl)oxy>-2-furanylethanol 在 palladium on activated charcoal sodium tetrahydroborate 、 cerium(III) chloride 、 4 A molecular sieve 、 三氟化硼乙醚 、 二苯基磷酸 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， -30.0~20.0 ℃ 、100.0 kPa 条件下， 反应 40.01h， 生成 (2S,3S,6R)-2-(tert-Butyldiphenylsilyloxymethyl)-6-ethoxy-1-tosylpiperidin-3-ol
  参考文献：
  名称：

  Transformation of d-Glucal to (2S)-Hydroxymethyl-dihydropyridones as Intermediates to Piperidine Alkaloids

  摘要：

  DOI：

  10.1055/s-1999-3604
• 作为产物：
  描述：

  6-O-(叔丁基二苯基甲硅烷基)-D-葡萄烯糖 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 Dibenzyl 2,3,4,6-tetra-O-acetyl-D-galactopyranosyl phosphite 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以69%的产率得到(2R) 1-<(t-butyldiphenylsilyl)oxy>-2-furanylethanol
  参考文献：
  名称：

  Glycosyl Phosphites as Glycosylation Reagents: Scope and Mechanism

  摘要：

  The glycosylation reactions with glycosyl phosphites in the presence of catalytic amounts of TMSOTf at low temperature have been studied with different donors and accepters for the synthesis of several glycosides, including O-glycosides, S-glycosides, C-glycosides, and glycopeptides. Mechanistic investigations of the reactions indicate that the glycosyl phosphite is activated by either TfOH or TMSOTf, depending on how the substrates are mixed. When the acceptor is treated with TMSOTf first, the glycosyl phosphite is activated by the resulting TfOH. The glycosyl phosphite can also be activated by TMSOTf directly. The best result is, however, to mix the acceptor and TMSOTf first, followed by addition of the glycosyl phosphite.

  DOI：

  10.1021/jo00083a032

文献信息

• Furan derivatives, method of synthesis and uses thereof
  申请人：Neuropharma S.A.

  公开号：EP1939191A1

  公开（公告）日：2008-07-02

  The present invention relates to furan derivatives of formula (I), their method of synthesis and uses thereof. Concretely, the compounds disclosed have proved to be inhibitors of glycogen synthase kinase 3β, GSK-3 β, which is known to be involved in different disease and conditions, such as Alzheimer's disease or non-insulin dependent diabetes mellitus. The present invention also relates to pharmaceutical compositions comprising the same. Further, the present invention is directed to the use of the compounds in the manufacture of a medicament for the treatment and/or prevention of a GSK-3 mediated disease or condition.

  本发明涉及式(I)的呋喃衍生物，其合成方法及用途。具体来说，所披露的化合物已被证明是糖原合成酶激酶3β（GSK-3β）的抑制剂，GSK-3β已知参与不同疾病和病况，如阿尔茨海默病或非胰岛素依赖型糖尿病。本发明还涉及包含这些化合物的药物组合物。此外，本发明旨在将这些化合物用于制造治疗和/或预防GSK-3介导的疾病或病况的药物。
• Catalytic tin radical mediated tricyclisations. Part 1. Monocyclisation studies †
  作者：David R. Kelly、Mark R. Picton

  DOI：10.1039/b000661k

  日期：——

  A general strategy for catalytic tin radical mediated, radical cascade reactions is proposed in which three rings are constructed in a single step. The initial step in the tricyclisation process has been examined using 2,3-dideoxy-α-D-erythro-hex-2-enopyranosides bearing unsaturated substituents at the 1-O and/or 4-O-positions. Substrates for cyclisation of substituents at the 1-O-position were prepared by a novel zinc chloride catalysed Ferrier rearrangement of tri-O-acetyl-D-glucal with unsaturated alcohols, whereas substrates for cyclisation of substituents at the 4-O-position were prepared by alkylation or acylation of ethyl 6-O-protected 2,3-dideoxy-α-D-erythro-hex-2-enopyranosides. Propargyl substituents cyclise efficiently, but propenyl substituents less so. Propioloyl substituents undergo hydrostannylation without cyclisation.

  提出了一种催化锡自由基介导的自由基级联反应的一般策略，其中在一步中构建了三个环。三环化过程的初始步骤是使用在1-O和/或4-O位具有不饱和取代基的2,3-脱氧-α-D-赤藓糖亨糖醛进行研究。用于1-O位取代基环化的底物是通过一种新型的氯化锌催化的Ferrier重排反应，将三-O-乙酰化的D-葡糖醛与不饱和醇反应而制备的，而用于4-O位取代基环化的底物则是通过烷基化或酰基化反应，对乙基6-O-保护的2,3-脱氧-α-D-赤藓糖亨糖醛进行处理。丙炔基取代基能有效环化，但丙烯基取代基则较差。丙炔酰基取代基在没有环化的情况下经历了氢锡化反应。
• Synthesis of (R)-Dihydropyridones as Key Intermediates for an Efficient Access to Piperidine Alkaloids
  作者：Evangelia Tzanetou、Konstantinos Kasiotis、Prokopios Magiatis、Serkos Haroutounian

  DOI：10.3390/12040735

  日期：——

  transformation of D-glucal to (2R)-hydroxymethyldihydropyridinone 5 in seven steps and 35 % overall yield is reported. Dihydropyridone 5 constitutes a versatile chiral building block for the synthesis of various piperidine alkaloids. In this regard, 5 was converted to piperidinol 13 and piperidinone 15, that may be further elaborated for the syntheses of (+)-desoxoprosophylline (1) and deoxymannojirimycin (3)

  据报道，D-葡糖醛分七步有效转化为 (2R)-羟甲基二氢吡啶酮 5，总产率为 35%。二氢吡啶酮 5 是合成各种哌啶生物碱的通用手性构件。在这方面，5 被转化为哌啶醇 13 和哌啶酮 15，它们可以分别用于 (+)-desoxoprosophylline (1) 和 deoxymannojirimycin (3) 或 D-甘露内酰胺 (4) 的合成。
• Chirality transfer from the furan ring transfer reaction
  作者：Yasuchika Yamaguchi、Noriaki Tatsuta、Kenji Hayakawa、Ken Kanematsu

  DOI：10.1039/c39890000470

  日期：——

  The furan ring transfer (FRT) reactions of optically active propynyl ethers [(1) and (2)] are described, facile chirality transfer from the cycloadduct to the allylic carbon of the product being observed; the stereochemistry of the product was determined by X-ray analysis.

  描述了光学活性丙炔醚[（1）和（2）]的呋喃环转移（FRT）反应，观察到从环加合物向产物的烯丙基碳的容易的手性转移；通过X射线分析确定产物的立体化学。
• Palladium‐Catalyzed Stereospecific <i>S</i>‐Glycosylation by Allylic Substitution
  作者：Yanyan Wang、Zhen Cao、Nengzhong Wang、Mingguo Liu、Haifeng Zhou、Long Wang、Nianyu Huang、Hui Yao

  DOI：10.1002/adsc.202300129

  日期：2023.5.23

  S-Glycosides are considerably more stable toward chemical degradation and enzymatic hydrolysis than O-glycosides, and thioglyco-peptides/proteins also demonstrate critical bioactivities in the living system. However, the general and stereoselective synthetic strategies are still challenging. Herein, a versatile S-glycosylation approach was developed by palladium-catalyzed allylic substitution to form

  S-糖苷比O-糖苷对化学降解和酶促水解更稳定，并且硫代糖肽/蛋白质在生命系统中也表现出关键的生物活性。然而，通用和立体选择性合成策略仍然具有挑战性。在此，通过钯催化的烯丙基取代开发了一种通用的S-糖基化方法，在温和条件下分别形成 α- 和 β- 硫代糖苷。可以耐受多种底物，以立体特异性方式提供硫糖苷，收率为 70%–86%。该协议还创建了对各种S连接二糖和糖肽的快速访问。