2,2’,3,3’,4,4’-hexa-O-acetyl-6,6’-dideoxy-6,6-diiodo-α,α-D-trehalose | 35014-74-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2’,3,3’,4,4’-hexa-O-acetyl-6,6’-dideoxy-6,6-diiodo-α,α-D-trehalose
• 英文别名: 6,6'-Dideoxy-6,6'-diiod-α,α-trehalose-hexaacetat；6,6'-Dideoxy-6,6'-dijod-hexa-O-acetyl-α,α-trehalose；6,6'-Diiod-6,6'-didesoxy-hexaacetyltrehalose；bis-(tri-O-acetyl-6-iodo-6-deoxy-α-D-glucopyranosyl)-ether；Bis-(tri-O-acetyl-6-jod-6-desoxy-α-D-glucopyranosyl)-aether；6,6 inverted exclamation marka-Diiodo-|A,|A-trehalose peracetate；[(2S,3S,4S,5R,6R)-4,5-diacetyloxy-2-(iodomethyl)-6-[(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-(iodomethyl)oxan-2-yl]oxyoxan-3-yl] acetate
• CAS: 35014-74-5
• 化学式: C₂₄H₃₂I₂O₁₅
• 分子量: 814.318
• InChiKey: YDAGLNWPAWOWNG-FXPCSOOLSA-N

物化性质

• 沸点：
  669.4±55.0 °C(Predicted)
• 密度：
  1.75±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  185.49
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  2,2’,3,3’,4,4’-hexa-O-acetyl-6,6’-dideoxy-6,6-diiodo-α,α-D-trehalose 在 苄胺 、 盐酸 、 氢气 、 palladium(II) hydroxide 作用下， 生成 6-氨基-6-脱氧-alpha-D-吡喃葡萄糖基6-氨基-6-脱氧-alpha-D-吡喃葡萄糖苷
  参考文献：
  名称：

  PROCESS FOR THE PRODUCTION OF DATH AND INTERMEDIATES THEREOF

  摘要：

  The present technology is direct to methods of producing 6,6′-diamino-6,6′-deoxy-trehalose (“DATH”) or a salt thereof. The methods include optionally protecting one or more hydroxyl groups of D-trehalose and converting the primary hydroxyl groups of D-trehalose to product DATH or a salt thereof through use of a halogen, azide, and/or protected amine to. The present technology is also direct to intermediate products of the methods.

  公开号：

  US20220389044A1
• 作为产物：
  描述：

  2,2',3,3',4,4'-hexa-O-acetyl-6,6'-bis-O-(4-toluenesulfonyl)-α,α'-trehalose 在 丙酮 、 sodium iodide 作用下， 生成 2,2’,3,3’,4,4’-hexa-O-acetyl-6,6’-dideoxy-6,6-diiodo-α,α-D-trehalose
  参考文献：
  名称：

  Bredereck, Chemische Berichte, 1930, vol. 63, p. 959,964

  摘要：

  DOI：

文献信息

• Synthetic assembly of two β-cyclodextrins through a trehalose moiety as a linker
  作者：Yoshihiro Ishimaru、Yosuke Saito、Yoko S. Shiraishi、Yasuaki Esumi、Daiyo Terunuma、Hiroyoshi Kuzuhara、Koji Matsuoka

  DOI：10.1016/j.tetlet.2021.153287

  日期：2021.8

  Synthetic assembly of two β-cyclodextrins (CDs) was efficiently accomplished using a 6,6′-di-iodotrehalose derivative as a unique linker by means of a one-pot reaction in liquid ammonia for Birch reduction and subsequent SN2 replacement. The unique sulfide-linked CD dimer displayed a wider hydrophobic region due to the cavity of the CDs and a part of similar structure of a trehalose linker. An inclusion

  合成的组件2β环糊精（CDS），使用6,6'-二iodotrehalose衍生物作为一个独特的接头由在用于Birch还原和随后的S液位氨一锅反应的方式被有效地完成Ñ 2更换。由于CD的空腔和海藻糖接头的相似结构的一部分，独特的硫化物连接的CD二聚体显示出更宽的疏水区域。使用 TNS（2-对甲苯胺基萘-6-磺酸盐）作为模型客体化合物，初步检查了 CD 二聚体的包含特性。
• Effects of Trehalose Polycation End-Group Functionalization on Plasmid DNA Uptake and Transfection
  作者：Kevin Anderson、Antons Sizovs、Mallory Cortez、Chris Waldron、D. M. Haddleton、Theresa M. Reineke

  DOI：10.1021/bm300471n

  日期：2012.8.13

  In this study, we have synthesized six analogs of a trehalose-pentaethylenehexamine glycopolymer (Tr4) that contain (1A) adamantane, (1B) carboxy, (1C) alkynyl-oligoethyleneamine, (1D) azido trehalose, (1E) octyl, or (1F) oligoethyleneamine end groups and evaluated the effects of polymer end group chemistry on the ability of these systems to bind, compact, and deliver pDNA to cultured HeLa cells. The polymers were synthesized in one pot azide-alkyne cycloaddition reactions with an adaptation of the Carothers equation for step growth polymerization to produce a series of polymers with similar degrees of polymerization. An excess of end-capping monomer was added at the end of the polymerizations to maximize functionalization efficiency, which was evaluated with GPC, NMR, and MALDI-TOF. The polymers were all found to bind and compact pDNA at similarly low N/P ratios and form polyplexes with plasmid DNA. The effects of the different end group structures were most evident in the polyplex internalization and transfection assays in the presence of serum as determined by flow cytometry and luciferase gene expression, respectively. The Tr4 polymers end capped with carboxyl groups (1B) (N/P = 7), octyne (1E) (N/P = 7), and oligoethyleneamine (1F) (N/P = 7), were taken into cells as polyplex and exhibited the highest levels of fluorescence, resulting from labeled plasmid. Similarly, the polymers end-functionalized with carboxyl groups (1E at N/P = 7), octyl groups (1E at N/P = 15), and in particular oligoethyleneamine groups (1F at N/P = 15) yielded dramatically higher reporter gene expression in the presence of serum. This study yields insight into how very subtle structural changes in polymer chemistry, such as end groups can yield very significant differences in the biological delivery efficiency and transgene expression of polymers used for pDNA delivery.