1-甲氧基-2,3,5-三乙酰氧基-D-呋喃核糖苷 | 52554-28-6

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-甲氧基-2,3,5-三乙酰氧基-D-呋喃核糖苷
• 英文名称: 2,3,5-tri-O-acetyl-1-O-methylglycoside
• 英文别名: 2,3,5-triacetyl-1-methoxyribofuranose；methyl 2,3,5-tri-O-acetyl-D-ribofuranoside；(2R,3R,4R)-2-(acetoxymethyl)-5-methoxytetrahydrofuran-3,4-diyl diacetate；Methyl-；tri-O-acetyl methyl α, β-ribofuranoside；[(2R,3R,4R)-3,4-diacetyloxy-5-methoxyoxolan-2-yl]methyl acetate
• CAS: 52554-28-6
• 化学式: C₁₂H₁₈O₈
• 分子量: 290.27
• InChiKey: RUSRQHXGPHZZNI-KBIHSYGRSA-N

物化性质

• 溶解度：
  可溶于氯仿、二氯甲烷、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  1-甲氧基-2,3,5-三乙酰氧基-D-呋喃核糖苷 在 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以40%的产率得到2,3,5-三-O-乙酰基-1,4-脱水-D-核糖醇
  参考文献：
  名称：

  一种合成脱水醛糖醇的改进方法

  摘要：

  据报道，通过乙酰化碳水化合物的还原裂解，脱水醛糖醇的合成得到改善。该过程似乎具有普遍性。没有观察到环重排，这使制备脱水醛糖醇的其他一些报道的过程复杂化。所用的乙酸酯保护基在所用的反应条件下是稳定的。

  DOI：

  10.1016/0040-4039(95)00618-m
• 作为产物：
  描述：

  D-吡喃核糖 在 吡啶 、 硫酸 作用下， 反应 4.0h， 生成 1-甲氧基-2,3,5-三乙酰氧基-D-呋喃核糖苷
  参考文献：
  名称：

  Glycosides and Glycoconjugates of the Diterpenoid Isosteviol with a 1,2,3-Triazolyl Moiety: Synthesis and Cytotoxicity Evaluation

  摘要：

  Several glycoconjugates of the diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) with a 1,2,3-triazolyl moiety were synthesized, and their cytotoxicity was evaluated against some human cancer and normal cell lines. Most of the synthesized compounds demonstrated weak inhibitory activities against the M-HeLa and MCF-7 human cancer cell lines. Three lead compounds, 54, 56 and 57, exhibited high selective cytotoxic activity against M-HeLa cells (IC50 = 1.7-1.9 mu M) that corresponded to the activity of the anticancer drug doxorubicin (IC50 = 3.0 mu M). Moreover, the lead compounds were not cytotoxic with respect to a Chang liver human normal cell line (IC50 > 100 mu M), whereas doxorubicin was cytotoxic to this cell line (IC50 = 3.0 mu M). It was found that cytotoxic activity of the lead compounds is due to induction of apoptosis proceeding along the mitochondrial pathway. The present findings suggest that 1,2,3-triazolyl-ring-containing glycoconjugates of isosteviol are a promising scaffold for the design of novel anticancer agents.

  DOI：

  10.1021/acs.jnatprod.0c00134

文献信息

• Highly Stereoselective Glycosylation Reactions of Furanoside Derivatives via Rhenium (V) Catalysis
  作者：Emanuele Casali、Sirwan T. Othman、Ahmed A. Dezaye、Debora Chiodi、Alessio Porta、Giuseppe Zanoni

  DOI：10.1021/acs.joc.1c00706

  日期：2021.6.4

  approach for the formation of anomeric carbon-functionalized furanoside systems was accomplished through the employment of an oxo-rhenium catalyst. The transformation boasts a broad range of nucleophiles including allylsilanes, enol ethers, and aromatics in addition to sulfur, nitrogen, and hydride donors, able to react with an oxocarbenium ion intermediate derived from furanosidic structures. The excellent

  通过使用氧代铼催化剂，实现了一种形成异头碳官能化呋喃糖苷系统的新方法。该转变拥有广泛的亲核试剂，包括烯丙基硅烷、烯醇醚和芳烃以及硫、氮和氢化物供体，能够与源自呋喃糖苷结构的氧代碳鎓离子中间体反应。观察到的优异立体选择性遵循 Woerpel 模型，最终提供 1,3-顺式-1,4-反式系统。在富电子芳香亲核试剂的情况下，平衡发生在异头中心，选择性形成 1,3-反式-1,4-顺式系统。这个异常结果通过密度泛函理论计算得到了合理化。不同的氧代碳鎓离子，例如衍生自二氢异苯并呋喃、吡咯烷和恶唑烷杂环的那些，也可用作氧代-Re 介导的烯丙基化反应的底物。
• N-d-Aldopentofuranosyl-N′-[p-(isoamyloxy)phenyl]-thiourea derivatives: Potential anti-TB therapeutic agents
  作者：Avraham Liav、Shiva K. Angala、Patrick J. Brennan、Mary Jackson

  DOI：10.1016/j.bmcl.2008.03.033

  日期：2008.4

  Thiocarlide (THC; N,N'-bis[p-(isoamyloxy)phenyl]-thiourea; also known as isoxyl) has been used in the past as anti-tuberculosis agent. In an effort to improve the therapeutic value of THC several N-pentofuranosyl-N'-[p-(isoamyloxy)phenyl]-thiourea derivatives were synthesized by coupling of an aniline derivative and pentofuranosyl isothiocyanates. The MIC values of the new products against M.tb indicate

  过去，硫代卡利特（THC； N，N'-双[对-（异戊氧基）苯基]-硫脲；也称为异氧基）已被用作抗结核药。为了提高THC的治疗价值，通过苯胺衍生物和戊呋喃糖基异硫氰酸酯的偶联，合成了几种N-戊呋喃糖基-N′-[对-（异戊氧基）苯基]-硫脲衍生物。新产品针对M.tb的MIC值表明，这种合成潜在抗结核病治疗剂的新方法是成功的。
• Process and intermediate compounds for the preparation of pyrrolidines
  申请人：Michigan State University Board of Trustees operating

  公开号：US20020019542A1

  公开（公告）日：2002-02-14

  Processes for the preparation of pyrrolidones (7 and 8) and pyrrolidines (9 and 10) from tri-O-acetyl-D-erythro-4-pentulosonic acid esters are described. The compounds are aza sugar analogs of D-ribofuranoside and are intermediates to drugs which regulate nucleoside and nucleic acid synthesis.

  本文描述了从三-O-乙酰-D-erythro-4-戊糖酸酯制备吡咯烷酮（7和8）和吡咯烷（9和10）的过程。这些化合物是D-核糖呋喃苷的氮杂糖类似物，是调节核苷酸和核酸合成的药物的中间体。
• Oxidation of Acetylated Guanosine by 3,3-Disubstituted 1,2-Dioxetanes through Nucleophilic Attack on the Peroxide Bond: Model Studies on the Oxidative DNA Damage by Reactive Peroxides
  作者：Waldemar Adam、Alexander Treiber

  DOI：10.1021/ja00115a002

  日期：1995.3

  The reaction of the disubstituted 3-(methoxymethyl)-3-phenyl-1,2-dioxetane (1a) with the acetylated guanine nucleoside (2) in methanol affords 8-methoxyguanosine 5 as oxidation product, as well as guanine (6) and 1-methoxyribose 7 by deglycosylation (total yield ca. 30%). The dioxetane-derived reduction product constitutes the 1,2-diol 40, while the major dioxetane-derived product (85%) is omega-methoxyacetophenone (3a). A Grob-type fragmentation is made responsible for the exclusive formation of the dioxetane cleavage products in the reactions with the acetylated nucleosides 8-10 derived from adenine, cytosine, and thymine. Rather than redox chemistry, this guanosine oxidation, unprecedented for peroxides, is proposed to involve nucleophilic attack by the N-7 atom of the nucleosides on the peroxide bond of the dioxetane la electrophile to generate a zwitterionic intermediate. S(N)2 attack by methanol at the C-8 position of the guanine moiety in the zwitterionic intermediate leads to the 8-methoxyguanosine 5 and the diol 4a. Alternatively, heterolytic cleavage of the glycosidic bond affords the methoxylated ribose 7 (after methanol trapping) and the N-7-alkoxylated guanine. The latter, after protonation, subsequently undergoes Grob fragmentation into guanine (6) and the dioxetane decomposition products omega-methoxyacetophenone (3a) and formaldehyde. We propose that the present novel oxidation of guanosine is general for electrophilic peroxides and may constitute a prominent route of oxidative DNA damage. In contrast, the corresponding 3-(bromethyl)-3-phenyl- 1,2-dioxetane (1b) gave with the guanosine 2 an intractable, complex product mixture, for which presumably the bromo substituent is responsible on account of competitive alkylation chemistry. However, with the 2'-deoxythymidine 10, a novel acid-catalyzed ring-opening of the bromo-substituted dioxetane Ib to its beta-methoxy hydroperoxide 11b is observed, a reaction which does not take place for the methoxy-substituted dioxetane 1a. This unusual process for simple dioxetanes is rationalized in terms of stabilization of the intermediary benzylic cation by the adjacent beta-bromo substituent through neighboring group participation.
• <i>Candida antarctica</i>B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides
  作者：Esteban D. Gudiño、Adolfo M. Iribarren、Luis E. Iglesias

  DOI：10.3109/10242422.2010.501105

  日期：2010.7

  Candida antarctica B lipase (CAL-B) catalysed alcoholysis of a series of peracetylated alkyl alpha, beta-D-ribofuranosides was assayed. Methyl and ethyl 2,3-di-O-acetyl-alpha, beta-D-ribofuranosides enriched in the alpha-anomer were regioselectively prepared through this enzymatic deacetylation in 33% and 43% yield, respectively, the latter being a new compound. Isopropyl 2,3,5-tri-O-acetyl-beta-D-ribofuranoside gave the new isopropyl 2,3-di-O-acetyl-beta-D-ribofuranoside in 24% yield. The anomeric substituent affects the regioselectivity of the reaction, since n-propyl and n-butyl alpha, beta-D-ribofuranosides reacted without selectivity.