2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl iodide | 188406-40-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl iodide
• 英文别名: 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl iodide；Glc2Ac3Ac4Ac6Ac(a1-4)a-Glc1I2Ac3Ac6Ac；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-iodooxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 188406-40-8
• 化学式: C₂₆H₃₅IO₁₇
• 分子量: 746.458
• InChiKey: ARLZWVYQLPEXJD-DEZPWFOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  44
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  212
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl iodide 在 四丁基溴化铵 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.0h， 生成 2-(5-hydroxyl-4H-pyran-4-one)-methyl-α-D-glucopyranosyl-(1→4)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Efficient synthesis of thioglycosylated kojic acid bys-glycosyl isothiouronium salts

  摘要：

  In this study, 7-S-glycosides of kojic acid were designed and synthesized as mimics of its 7-O-glycosides to improve its water solubility and metabolic stability. To achieve this synthesis, a one-pot approach involving S-glycosyl isothiouronium salts generated in situ as key intermediates was developed by using 7-chloro-kojic acid as the alkylation reagent. A series of water soluble 7-S-glycosides of kojic acid, incorporating monosaccharides and disaccharides, were prepared using this protocol. Thus, this work offers a mild, convenient, and efficient approach for the synthesis of 7-S-glycosides of kojic acid in medium to good yields.[GRAPHICS].

  DOI：

  10.1080/07328303.2016.1261881
• 作为产物：
  描述：

  麦芽糖 在 三乙基硅烷 、 碘 、 sodium acetate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl iodide
  参考文献：
  名称：

  寡糖附加的水杨醛的途径：合成金属–盐酚配合物的有用组成部分

  摘要：

  本文报道了一种简单而通用的合成方法，用于获得寡糖附加的水杨醛，水杨醛是合成水溶性金属-烯丙基酚配合物的关键中间体。已经制备并充分表征了六种新的醛，以及相应的锌-和铀基-salophen配合物。这些新的衍生物在水中显示出非常好的溶解性。对化合物19-U（即铀酰麦芽四糖衍生物）与磷酸氢根和氟化物的缔合的初步研究提供了非常令人鼓舞的结果，并开辟了使用此类化合物有效识别纯水中阴离子的可能性。

  DOI：

  10.1021/jo401148f

文献信息

• Convenient, in Situ Generation of Anhydrous Hydrogen Iodide for the Preparation of α-Glycosyl Iodides and Vicinal Iodohydrins and for the Catalysis of Ferrier Glycosylation
  作者：Stephanie M. Chervin、Paolo Abada、Masato Koreeda

  DOI：10.1021/ol991312d

  日期：2000.2.1

  [reaction: see text] Anhydrous hydrogen iodide is generated in situ by the reaction of solid iodine and a thiol. The HI thus generated has been employed for the efficient preparation of alpha-glycosyl iodides and vicinal iodohydrins from the corresponding glycosyl acetates and epoxides, respectively, and for Ferrier glycosylation of alcohols and thiols.

  [反应：见正文]无水碘化氢是通过固体碘与硫醇的反应原位生成的。由此产生的HI已被用于分别从相应的乙酸糖基酯和环氧化物有效地制备α-糖基碘化物和邻位碘代醇，以及用于醇和硫醇的ferrier糖基化。
• A convenient synthesis of peracetylated glycosyl halides using bismuth(III) halides as catalysts
  作者：Jean-Louis Montero、Jean-Yves Winum、Alain Leydet、Mehrnaz Kamal、André A Pavia、Jean-Pierre Roque

  DOI：10.1016/s0008-6215(96)00269-8

  日期：1997.1

  Abstract A new halogenation procedure for peracetylated glycopyranosides is reported, using bismuth(III) halides and halogenosilanes under very mild conditions. © 1997 Elsevier Science Ltd.

  摘要报道了一种在非常温和的条件下使用卤化铋（III）和卤代硅烷对全乙酰基吡喃葡萄糖苷进行卤化的新方法。©1997爱思唯尔科学有限公司。
• Halogenation and anomerization of glycopyranoside by <scp>TESH</scp> /bromine and <scp>BHQ</scp> /bromine
  作者：Lai Xu、Chin‐Hung Luo、Chien‐Sheng Chen

  DOI：10.1002/jccs.202000150

  日期：2021.2

  Treatment of peracetylated glycosides and β‐isopropyl glycosides with halogen in the presence of TESH and BHQ has been found to result in the halogenation and the anomerization, respectively. Peracetylatedglycosides treaded with I2/TESH or Br2/TESH leading tothe formation of corresponding glycosyl halides, and b‐isopropyl glycosidesreacted with Br2/BHQ resulting in the formation of a‐glycosides. The

  已经发现在TESH和BHQ存在下用卤素处理过乙酰化的糖苷和β-异丙基糖苷分别导致卤化和异构化。过乙酰化的糖苷与I2 / TESH或Br2 / TESH结合使用会导致形成相应的糖基卤化物，而b-异丙基糖苷与Br2 / BHQ反应会导致a-糖苷的形成。糖苷键的异构化被认为是由Br2 / BHQ的混合原位形成溴化氢所催化的。
• Facile Preparation of α-Glycosyl Iodides by In Situ Generated Aluminum Iodide: Straightforward Synthesis of Thio-, Seleno-, and <i>O</i>-glycosides from Unprotected Reducing Sugars
  作者：Shiue-Shien Weng、Chia-Ling Li、Chun-Sheng Liao、Ting-An Chen、Chao-Cheih Huang、Kuo-Tung Hung

  DOI：10.1080/07328303.2011.565894

  日期：2010.11.1
• Streamlined Synthesis of Per-<i>O</i>-acetylated Sugars, Glycosyl Iodides, or Thioglycosides from Unprotected Reducing Sugars¹
  作者：Balaram Mukhopadhyay、K. P. Ravindranathan Kartha、David A. Russell、Robert A. Field

  DOI：10.1021/jo048890e

  日期：2004.10.1

  Solvent-free per-O-acetylation of sugars with stoichiometric acetic anhydride and catalytic iodine proceeds in high yield (90-99%) to give exclusively pyranose products as anomeric mixtures. Without workup, subsequent anomeric substitution employing iodine in the presence of hexamethyldisilane (i.e., TMS-I generated in situ) gives the corresponding glycosyl iodides in 75-95% isolated yield. Alternatively, and without workup, further treatment with dimethyl disulfide or thiol (ethanethiol or thiocresol) gives anomerically pure thioglycosides in more than 75% overall yield.