benzyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside | 155681-03-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside
• 英文别名: (3aR,4R,6S,6aR)-2,2-dimethyl-4-phenylmethoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carbaldehyde
• CAS: 155681-03-1
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: OGBMDKPBMYYRMN-AAVRWANBSA-N

物化性质

• 沸点：
  389.2±42.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside 在 palladium on activated charcoal 4-二甲氨基吡啶 、 sodium hydroxide 、 硼烷四氢呋喃络合物 、 氢气 、 双氧水 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醇 为溶剂， 反应 27.5h， 生成
  参考文献：
  名称：

  Simple approach to O-protected deaminotunicaminyluracil

  摘要：

  A five-step synthesis of deaminotunieaminyluracil is presented. Coupling of the ylide, generated from the phosphonium salt 4, with the aldehyde 5 afforded the undecose 6 in high yield. The key step in this synthesis was the hydroboration-oxidation reaction of the olefin 6. For this purpose several hydroborating reagents were examined. The diborane-THF reagent led to the desired deaminotunicamine derivative 8, as the predominant product. Condensation of undecose 8c with 1,3-di-O-trimethylsilyluracil gave the title compound.

  DOI：

  10.1016/s0040-4020(01)87008-3
• 作为产物：
  描述：

  benzyl 2,3-O-isopropylidene-D-ribofuranoside 在 重铬酸吡啶 作用下， 以70%的产率得到benzyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside
  参考文献：
  名称：

  苄基2,3 - O-异亚丙基-β-D-核糖-1,4-戊二醛呋喃糖苷作为D-核糖Chiron的合成萜烯四醇和氨基三醇

  摘要：

  标题化合物与衍生自R -（+）-柠檬烯的膦烷的Wittig缩合，然后进行催化氢化，提供了C-5扩展的呋喃核糖衍生物，这是通过NaBH 4还原合成萜烯四醇的模型中间体，而萜烯基氨基三醇通过重铬酸吡啶鎓的连续氧化，氨解和LiAlH 4还原。

  DOI：

  10.1016/0040-4039(95)00483-s

文献信息

• Synthesis of 4- and 5-(<i>s</i>-triazolo[4,3-<i>b</i>]pyridazinyl-3)-substituted cyclic polyols
  作者：Cvetka Turk、Jury Svete、Amalija Golobič、Ljubo Golič、Branko Stanovnik

  DOI：10.1002/jhet.5570350304

  日期：1998.5

  4(R)-(6-Chloro-s-triazolo[4,3-b]pyridazinyl-3)-1,4-furanoses 10 and 11, 5(R)-(6-chloro-s-triazolo[4,3-b]pyridazinyl-3)-1,5-pyranose 13, and 2(S),3(R)-dihydro-5-(6-chloro-s-triazolo[4,3-b]pyridazinyl-3)-2,3-O-isopropylidenefuran (12) were prepared by cyclization of hydrazones 6–9 obtained from 6-chloro-3-hydrazinopyridazine (1) and aldofuranoses 2, 3 and 4, and aldopyranose 5.

  4（[R ）- （6-氯-小号-三唑并[4,3- b ]哒嗪基-3-基）-1,4-呋喃糖10和11，图5（[R ）- （6-氯-小号-三唑并[4， 3- b ]哒嗪基-3-）-1,5-吡喃糖13，和2（小号），3（[R ）-二氢-5-（6-氯-小号-三唑并[4,3- b ]哒嗪基-3） -2,3- O-异亚丙基呋喃（12）是通过将6-氯-3-肼基哒嗪（1）和醛呋喃糖酶2、3和4所得到的6 6–9环化而制备的和aldopyranose 5。
• Stereoselective syntheses of the O,N-protected subunits of the tunicamycins
  作者：Wojciech Karpiesiuk、Anna Banaszek

  DOI：10.1016/s0008-6215(97)00018-9

  日期：1997.4

  The synthesis of the title compounds is described, i.e. coupling of the ylide, generated from the iodophosphonium salt of protected N-phthaloyl-D-galactosamine with 2,3-O-isopropylidene D-ribo-aldehyde afforded an undecose in high yield. Hydroboration-oxidation reaction of the olefinic linkage in the undecose led to the desired tunicamine, as the predominant product. After conversion of the latter

  描述了标题化合物的合成，即，由保护的N-邻苯二甲酰基-D-半乳糖胺的碘鎓盐与2,3-O-异亚丙基D-核糖醛偶联生成的叶立德以高收率得到十一糖。十一烷中的烯键的氢硼化-氧化反应产生了作为主要产物的所需丁二胺。在后者转化为糖基受体之后，将其与完全保护的2-氧亚氨基-2-脱氧-α-D-阿拉伯糖基-己吡喃糖基溴组装，得到海藻糖型α，β-二糖。
• Complex Biohopanoids Synthesis: Efficient Anchoring of Ribosyl Subunits onto a C30 Hopane
  作者：Weidong Pan、Chao Sun、Yongmin Zhang、Guangyi Liang、Pierre Sinaÿ、Stéphane P. Vincent

  DOI：10.1002/chem.200600659

  日期：2007.2.2

  through a C--C bond. The biological function of biohopanoids also has to be addressed when one considers the broad diversity in both structures and functionalities found in the side chain. Moreover, the stereochemistries of some biohopanoids are still unconfirmed, due to the lack of synthetic methods to prepare them. In this study we describe an efficient methodology for the formation of the C--C bond

  细菌类胡萝卜素代表了一个特别重要的三萜类化合物系列，广泛分布于细菌中。这些五环hop烷多元醇的共同特征之一是存在延伸的非萜类和多羟基化侧链，这些侧链通过CC键与三萜部分相连。当人们考虑侧链中结构和功能的广泛多样性时，也必须解决生物类胡萝卜素的生物学功能。此外，由于缺乏合成类胡萝卜素的合成方法，某些类生物类胡萝卜素的立体化学仍未得到证实。在这项研究中，我们描述了一种通过使用a基锂中间物在C（30）-戊烷组分和C（5）-多羟基化碳水化合物之间形成C-C键的有效方法，这使我们能够合成几种生物类类胡萝卜素衍生物。我们还报告了在位置C31处带有一个额外羟基的hop烷戊醇的首次合成。
• Direct Catalytic Stereoselective Synthesis of C4′ Functionalized Furanoside and Nucleoside Derivatives with a Tetrasubstituted Stereocenter
  作者：Kaiheng Zhang、Haibo Wu、A. Ken Inge、Armando Córdova

  DOI：10.1002/adsc.202301509

  日期：2024.5.21

  direct entry to C4’-functionalized furanoside derivatives with a tetrasubstituted stereocenter by a novel amine-catalyzed stereoselective α-aminomethylation transformation of furanoside C5’ aldehyde derivatives 1 (Scheme 2d). However, the important generation of tetrasubstituted stereocenters is a challenging task in organic chemistry.11 Herein a novel direct catalytic stereoselective entry to C4’-functionalized

  核苷是生命的基础，是 DNA 或 RNA 的分子组成部分。核苷的结构由呋喃糖（例如核糖）和含氮碱基组成。核苷的合成涉及杂环碱基与亲电子呋喃糖的偶联，其中最常见的方法是 Vorbrüggen 反应。 1 核苷类似物可以具有 D-或 L-绝对构型，旨在模拟天然核苷的活性，用于重要应用，例如用于抑制病毒的 DNA 或 RNA 干扰。 2 因此，它们是抗病毒药物开发的重要来源。只需对核苷结构进行微小的修改即可对其代谢活性和构象刚性产生巨大影响。事实上，呋喃糖苷部分的 C1'、C2'、C3' 或 C4' 位点的功能化导致了核苷 2b, 2c 的合成，其可作为具有抗病毒和抗癌活性的药物（图 1） 。例如，瑞德西韦是一种用于治疗 COVID-19 的广谱抗病毒药物。  图1 在图查看器中打开PowerPoint 核苷类似物的例子。 特别是，呋喃糖苷部分 C4' 的修饰具有挑战性，迫切需要开发催化工艺。 2f
• <i>N</i>-Alkyl-, 1-<i>C</i>-Alkyl-, and 5-<i>C</i>-Alkyl-1,5-dideoxy-1,5-imino-(<scp>l</scp>)-ribitols as Galactosidase Inhibitors
  作者：Sophie Front、Estelle Gallienne、Julie Charollais-Thoenig、Stéphane Demotz、Olivier R. Martin

  DOI：10.1002/cmdc.201500485

  日期：2016.1

  AbstractA series of 1,5‐dideoxy‐1,5‐imino‐(l)‐ribitol (DIR) derivatives carrying alkyl or functionalized alkyl groups were prepared and investigated as glycosidase inhibitors. These compounds were designed as simplified 4‐epi‐isofagomine (4‐epi‐IFG) mimics and were expected to behave as selective inhibitors of β‐galactosidases. All compounds were indeed found to be highly selective for β‐galactosidases versus α‐glycosidases, as they generally did not inhibit coffee bean α‐galactosidase or other α‐glycosidases. Some compounds were also found to be inhibitors of almond β‐glucosidase. The N‐alkyl DIR derivatives were only modest inhibitors of bovine β‐galactosidase, with IC50 values in the 30–700 μm range. Likewise, imino‐l‐ribitol substituted at the C1 position was found to be a weak inhibitor of this enzyme. In contrast, alkyl substitution at C5 resulted in enhanced β‐galactosidase inhibitory activity by a factor of up to 1000, with at least six carbon atoms in the alkyl substituent. Remarkably, the ‘pseudo‐anomeric’ configuration in this series does not appear to play a role. Human lysosomal β‐galactosidase from leukocyte lysate was, however, poorly inhibited by all iminoribitol derivatives tested (IC50 values in the 100 μm range), while 4‐epi‐IFG was a good inhibitor of this enzyme. Two compounds were evaluated as pharmacological chaperones for a GM1‐gangliosidosis cell line (R301Q mutation) and were found to enhance the mutant enzyme activity by factors up to 2.7‐fold.