1-β-formyl-3-α-hydroxy-3-β-allyl-4α,5α-O-isopropylidene-tetrahydrofuran | 136152-94-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-β-formyl-3-α-hydroxy-3-β-allyl-4α,5α-O-isopropylidene-tetrahydrofuran
• 英文别名: 1,2-O-isopropylidene-3-C-(prop-1-en-3-yl)-α-D-ribo-pentodialdo-1,4-furanose；(3aR,5S,6R,6aR)-6-hydroxy-2,2-dimethyl-6-prop-2-enyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole-5-carbaldehyde
• CAS: 136152-94-8
• 化学式: C₁₁H₁₆O₅
• 分子量: 228.245
• InChiKey: SJHIMJXHSIQSHS-PKIKSRDPSA-N

物化性质

• 沸点：
  329.7±42.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-β-formyl-3-α-hydroxy-3-β-allyl-4α,5α-O-isopropylidene-tetrahydrofuran 在 吡啶 、 potassium osmate(VI) dihydrate 、 sodium tetrahydroborate 、 sodium periodate 、 sodium cyanoborohydride 、 碳酸氢钠 、 溶剂黄146 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  γ-Hydroxyethyl piperidine iminosugar and N-alkylated derivatives: A study of their activity as glycosidase inhibitors and as immunosuppressive agents

  摘要：

  An efficient and practical strategy for the synthesis of (3R, 4s, 5S)-4-(2-hydroxyethyl) piperidine-3,4,5-triol and its N-alkyl derivatives 8a-f, starting from the D-glucose, is reported. The chiral pool methodology involves preparation of the C-3-allyl-alpha-D-ribofuranodialdose 10, which was converted to the C-5-amino derivative 11 by reductive amination. The presence of C-3-allyl group gives an easy access to the requisite hydroxyethyl substituted compound 13. Intramolecular reductive aminocyclization of C-5 amino group with C-1 aldehyde provided the gamma-hydroxyethyl substituted piperidine iminosugar 8a that was N-alkylated to get N-alkyl derivatives 8b-f. Iminosugars 8a-f were screened against glycosidase enzymes. Amongst synthetic N-alkylated iminosugars, 8b and 8c were found to be a-galactosidase inhibitors while 8d and 8e were selective and moderate alpha-mannosidase inhibitors. In addition, immunomodulatory activity of compounds 8a-f was examined. These results were substantiated by molecular docking studies using AUTODOCK 4.2 programme. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.09.034
• 作为产物：
  描述：

  1',2'-O-isopropylidene-3'-C-(prop-1-enyl)-α-D-allyl-1',4'-furanose 在 sodium periodate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 1-β-formyl-3-α-hydroxy-3-β-allyl-4α,5α-O-isopropylidene-tetrahydrofuran
  参考文献：
  名称：

  获得光学活性，功能化的五元，六元和七元碳环衍生物的简单途径

  摘要：

  用作非天然生物活性手性碳环核苷和糖苷酶抑制剂的前体的异恶唑烷碳环衍生物6、7和13已经由D-葡萄糖通过分子内的1,3-偶极环加成合成。

  DOI：

  10.1016/0040-4020(96)00652-7

文献信息

• In situ 1,3-dipolar azide cycloaddition reaction: synthesis of functionalized d-glucose based chiral piperidine and oxazepine analogues
  作者：Subhankar Tripathi、Kaushik Singha、Basudeb Achari、Sukhendu B Mandal

  DOI：10.1016/j.tet.2004.04.036

  日期：2004.5

  Functionalized furanose-fused piperidines 4-6 and oxazepines 15-17, useful precursors for structurally unique bioactive nucleosides as well as for potential glycosidase inhibitors, have been synthesized by the application of 1,3-dipolar azide cycloaddition (DAC) reaction on d-glucose based substrates. The strategy works well even with the nucleoside analogue 8, affording the bicyclic nucleoside analogues

  官能呋喃稠合的哌啶4 - 6和氧氮杂15 - 17，以及潜在的糖苷酶抑制剂，已经通过1,3-偶极环加成的叠氮化物（DAC）反应的应用上D-合成为结构独特的生物活性的核苷前体的有用的葡萄糖基底物。该策略即使与核苷类似物8一起也能很好地工作，提供双环核苷类似物11和12。
• Synthesis of an Adenine Nucleoside Containing the (8′<i>R</i>) Epimeric Carbohydrate Core of Amipurimycin and Its Biological Study
  作者：Rajendra S. Mane、Sougata Ghosh、Balu A. Chopade、Oliver Reiser、Dilip D. Dhavale

  DOI：10.1021/jo102193q

  日期：2011.4.15

  The (8′R) epimeric carbohydrate core 2 of amipurimycin was synthesized from d-glucose derived allylic alcohol 3 in 11 steps and 13% overall yield. The key steps involve an acid-catalyzed acetonide ring opening of 9 with concomitant formation of an unprecedented pyranose ring skeleton to give 2,7-dioxabicyclo[3.2.1]octane 10. The α-orientation of the furan ring in 10 readily allows the stereoselective

  所述（8' - [R ）差向异构体的碳水化合物芯2 amipurimycin的合成自d葡萄糖衍生的烯丙醇3在11个步骤和13％的总收率。的关键步骤涉及酸催化的丙酮化合物开环9与伴随形成了前所未有的吡喃糖环骨架，得到2,7-二氧杂双环[3.2.1]辛烷的10。呋喃环在10中的α取向很容易实现呋喃糖环的立体选择性β-糖基化和打开，这在去除保护基团后即可得到吡喃糖基腺嘌呤核苷2。研究了2种的抗真菌和抗癌活性。
• Synthesis and biological evaluation of conformationally restricted adenine bicycloribonucleosides
  作者：Hubert Hřebabecký、Eliška Procházková、Michal Šála、Pavla Plačková、Eva Tloušťová、Ona Barauskas、Yu-Jen Lee、Yang Tian、Richard Mackman、Radim Nencka

  DOI：10.1039/c5ob00987a

  日期：——

  to 5′ methylene groups of the sugar. The bicyclonucleosides were also transformed to the corresponding phosphoramidate prodrugs by an innovative one-pot protocol of boronate ester protection, coupling of the phosphoryl chloridate and deprotection of the boronate. A similar strategy was also employed for the synthesis of the corresponding monophosphates as crucial intermediates for the synthesis of

  我们制备了一系列构象受限的双环核苷和核苷酸。合成方法采用闭环置换，以提供连接糖的3'至5'亚甲基的6和7元饱和和不饱和环的途径。通过创新性的一锅法硼酸酯保护，磷酰氯的偶联和硼酸酯的脱保护，双环核苷也被转化为相应的氨基磷酸酯前药。类似的策略也用于合成相应的单磷酸酯，作为合成选定的三磷酸酯的关键中间体。在基于细胞的测定中评估了核苷和单磷酸酯前药的生物学特性的抗病毒和细胞抑制活性，同时在酶促测定中评估了三磷酸酯。缺乏显着影响表明3'至5'的连锁通过环系统以及随后的核糖环构象限制为South构象与识别核苷及其代谢产物的激酶和聚合酶不相容。
• Strategies and tactics for free radical carbocyclization: synthesis of polyfunctionalized cyclopentanoid molecules from carbohydrates
  作者：José Marco-Contelles、Pilar Ruiz、Luis Martínez、Angeles Martínez-Grau

  DOI：10.1016/s0040-4020(01)81837-8

  日期：1993.7

  The tributyltin hydride + azobisisobutyronitrile (AIBN) mediated free radical carbocyclization of precursors 1-9, 48 and 49 is described. The resulting carbocycles have been obtained in moderate yield and good diastereoselectivity. These polyfunctionalized, enantiomerically pure cyclopentane derivatives are useful intermediates for further manipulation.
• Cyclization in situ of enose-/ynose-nitrilimines: an expedient approach to the synthesis of chiral glycopyrazoles and pyrazolonucleosides
  作者：Ashim Roy、Sk. Sahabuddin、Basudeb Achari、Sukhendu B. Mandal

  DOI：10.1016/j.tet.2004.10.096

  日期：2005.1

  Intramolecular [3 + 2] nitrilimine cycloaddition reactions on carbohydrate-derived substrates proceed in a regioselective fashion, affording structurally novel chiral glycopyrazoles (4-6 and 10a-c) in good yields. The products can be subsequently transformed to bicyclic pyrazoles (viz. 11 from 4) or nucleoside analogues (viz. 12 from 4). (C) 2004 Elsevier Ltd. All rights reserved.