acetoxy α-D-2,3,4-triacetoxy-6-deoxy-6-iodoglucopyranoside | 24871-54-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: acetoxy α-D-2,3,4-triacetoxy-6-deoxy-6-iodoglucopyranoside
• 英文别名: 1,2,3,4-tetra-O-acetyl-6-deoxy-6-iodo-α-D-glucopyranose；tetra-O-acetyl-6-iodo-6-deoxy-α-D-glucopyranose；Tetra-O-acetyl-6-jod-6-desoxy-α-D-glucopyranose；6-Desoxy-6-iod-1,2,3,4-tetra-O-acetyl-α-D-glucopyranose；6-Deoxy-6-iod-1,2,3,4-tetra-O-acetyl-α-D-glucopyranose；Tetra-O-acetyl-6-desoxy-6-iod-α-D-glucopyranose；alpha-D-Glucopyranose, 6-deoxy-6-iodo-, tetraacetate；[(2S,3S,4S,5R,6R)-4,5,6-triacetyloxy-2-(iodomethyl)oxan-3-yl] acetate
• CAS: 24871-54-3
• 化学式: C₁₄H₁₉IO₉
• 分子量: 458.204
• InChiKey: QSYWOQIXQODCDZ-RGDJUOJXSA-N

物化性质

• 熔点：
  180 °C(Solv: ethanol (64-17-5))
• 沸点：
  442.1±45.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  acetoxy α-D-2,3,4-triacetoxy-6-deoxy-6-iodoglucopyranoside 在 叠氮基三甲基硅烷 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-β-D-glucopyranosyl azide
  参考文献：
  名称：

  A General Synthesis of Iminosugars

  摘要：

  1-Deoxynojirimycin, 1-deoxymannojirimycin, and 1-deoxygalactostatin have been synthesized by epoxidation of tri-O-acetyl-6-deoxyhex-5-enopyranosyI azides followed by methanolysis, deacetylation, and catalytic hydrogenation. 1,6-Dideoxygalactostatin was obtained by the reaction of 2,3,4-tri-O-acetyl-6-deoxy-beta-L-arabino-hex-5-enopyranosyl azide with NIS in methanol followed by deacetylation and catalytic hydrogenation. The overall yields were 4.4-23.5% over seven to nine steps.

  DOI：

  10.1021/jo035763u
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 吡啶 、 咪唑 、 硫酸 、 碘 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 26.5h， 生成 acetoxy α-D-2,3,4-triacetoxy-6-deoxy-6-iodoglucopyranoside
  参考文献：
  名称：

  A General Synthesis of Iminosugars

  摘要：

  1-Deoxynojirimycin, 1-deoxymannojirimycin, and 1-deoxygalactostatin have been synthesized by epoxidation of tri-O-acetyl-6-deoxyhex-5-enopyranosyI azides followed by methanolysis, deacetylation, and catalytic hydrogenation. 1,6-Dideoxygalactostatin was obtained by the reaction of 2,3,4-tri-O-acetyl-6-deoxy-beta-L-arabino-hex-5-enopyranosyl azide with NIS in methanol followed by deacetylation and catalytic hydrogenation. The overall yields were 4.4-23.5% over seven to nine steps.

  DOI：

  10.1021/jo035763u

文献信息

• NaBH₃CN: A Janus Substitute for Tin-Free Radical-Based Reactions
  作者：Julie Guiard、Yaniss Rahali、Jean-Pierre Praly

  DOI：10.1002/ejoc.201402441

  日期：2014.7

  depending on the conditions, either by reductive cyclization or atom-transfer radical cyclization. A related cyclization occurred upon using Cu(OAc)2. This and other assays showed the reduction by NaBH3CN of CuII salts, either added or formed in situ. Having both ionic and radical reactivity, NaBH3CN appears as a Janus reagent that may be useful for tin-free radical chemistry under mild and very simple

  除了表明如果溴/碘糖用 NaBH3CN 和 2,2"-偶氮二异丁腈处理时热自由基反应（还原、Giese 反应）是有效的，我们还探索了基于 CuI 盐（≤0.5 当量）的新引发条件。通过一组从有机溴化物产生自由基。这已得到证实，因为在惰性气氛下，乙酰溴葡萄糖在约 50 °C 被还原为重排的 2-脱氧葡萄糖，并且随着 N-烯丙基 α-溴酰胺反应，取决于条件，通过还原环化或原子转移自由基环化。使用 Cu(OAc)2 时会发生相关的环化反应。该试验和其他试验表明，添加或原位形成的 CuII 盐被 NaBH3CN 还原。具有离子和自由基两种反应性，
• Difructose dianhydrides from sucrose and fructo-oligosaccharides and their use as building blocks for the preparation of amphiphiles, liquid crystals, and polymers
  作者：José Manuel García Fernández、Andrée Gadelle、Jacques Defaye

  DOI：10.1016/0008-6215(94)00239-8

  日期：1994.12

  derivatives of 2. Reaction of chloromethyloxirane with 1 or 2 yielded hydrophilic polymers. The 6,6'-di-S-heptyl-6,6'-dithio derivative of 1 displayed liquid crystal properties. The 6,6'-dideoxy-6,6'-diiodosucrose precursor was prepared by the reaction of Garegg's iodine-imidazole-triphenylphosphine reagent with sucrose in N,N-dimethylformamide solution.

  蔗糖和低聚果糖中的果糖基部分的选择性质子活化，在20摄氏度下用吡啶鎓聚（氟化氢）产生动力学产物α-D-果糖呋喃糖β-D-果糖呋喃糖1,2'：2,1 '-二酐（1）或其热力学更稳定的异构体α-D-果糖呋喃糖β-D-果糖吡喃糖1,2'：2,1'-二酐（2），具体取决于氟化氢与吡啶的比率。用6,6'-二氯-6,6'-二脱氧蔗糖或6,6'-二脱氧-6,6'-二碘蔗糖进行了类似的反应，只是使用了更高的HF比例，得到了相应的6-脱氧-6-卤代-α-D-果糖呋喃糖6'-脱氧-6'-卤代-β-D-果糖呋喃糖1,2'：2,1'-二酐衍生物。在适当的亲核试剂作用下，两种6,6'-二卤化物均被转化，进入带有6,6'-二-S-庚基-6,6'-二硫代，6,6'-二叠氮基-6,6'-二脱氧和然后6,6'-二氨基-6,6的二果呋喃糖二酐衍生物-二脱氧官能团。还通过直接卤化制备2的6-氯-6-脱氧和6-脱氧-6-碘衍生物
• The Synthesis of Various 1,6-Disulfide-Bridged D-Hexopyranoses
  作者：Ethan D. Goddard-Borger、Robert V. Stick

  DOI：10.1071/ch04277

  日期：——

  1,6-Disulfide-bridged derivatives have been prepared for d-gluco-, d-manno-, d-allo-, d-galacto-, and d-talo-pyranose, in the main by the nucleophilic attack of a C6 thiolate onto an anomeric thiosulfonate. The d-gluco disulfide, ‘angyalosan’, was successfully oxidized to a single thiosulfinate.

  1,6 二甲基二硫键衍生物的制备主要是通过 C6 硫代硫酸酯与异构体硫代磺酸酯的亲核反应，制备出了 d-葡糖、d-甘露糖、d-异甘露糖、d-半乳糖和 d-塔罗吡喃糖。d- 葡萄糖二硫化物 "anggyalosan "被成功氧化成单一的硫代亚硫酸盐。
• Synthesis of 1,3-Dithiole-2-thione-4,5-dithiolate-Carbohydrate Conjugate
  作者：Angelica Heinrich、Shahnaz Perveen、Khalid Khan、Gerardo Janairo、Gernot Bruchelt、Syed Shah、Wolfgang Voelter

  DOI：10.2174/157017809788489873

  日期：2009.6.1

  Bis(tetraethylammonium)bis(1,3-dithiole-2-thione-4,5-dithiolato) zincate (5), and 4,5-bis(cyanoethylthio)-1,3- dithiole-2-thione (6) were reacted with 6-deoxy-6-iodo-glucopyranose (2) and glucopyranosyl bromide (3) to synthesize DMIT-carbohydrate conjugates.

  双（四乙基铵）双（1,3-二硫代-2-硫酮-4,5-二硫醇）锌酸盐（5）和 4,5-双（氰乙基硫代）-1,3-二硫代-2-硫酮（6）与 6-脱氧-6-碘-吡喃葡萄糖（2）和溴化吡喃葡萄糖（3）反应，合成 DMIT-碳水化合物共轭物。
• Cyclic peptide antifungal agents
  申请人：——

  公开号：US20030125240A1

  公开（公告）日：2003-07-03

  The present invention relates to compounds of formula I: 1 where R 5 is a sugar moiety. The compounds are useful in inhibiting fungal and parasitic activity and infections.

  本发明涉及式I的化合物：1其中R5是糖基团。这些化合物在抑制真菌和寄生虫活性和感染方面非常有用。