Isomaltose octaacetat | 55700-65-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Isomaltose octaacetat
• 英文别名: isomaltose octaacetate；β-Isomaltose-octaacetat；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(2R,3R,4S,5R)-3,4,5,6-tetraacetyloxyoxan-2-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 55700-65-7
• 化学式: C₂₈H₃₈O₁₉
• 分子量: 678.598
• InChiKey: GNTLGGDVHFXGLI-XRGTYMDYSA-N

物化性质

• 熔点：
  175 °C(Solv: ethanol (64-17-5))
• 沸点：
  661.4±55.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.83
• 重原子数：
  47.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  238.09
• 氢给体数：
  0.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  Isomaltose octaacetat 在 palladium on activated charcoal 三氟化硼乙醚 、 氢气 、 氟化氢吡啶 、 三乙胺 作用下， 生成 O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1[*]6)-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosyl)-(1[*]6)-2,3,4-tri-O-acetyl-α-D-glucopyranosylamine
  参考文献：
  名称：

  Total synthesis of nephritogenic glycopeptide, nephritogenoside

  摘要：

  Nephritogenoside (1), proposed as a nephritogenic triglycosylhenicosapeptide with asparagine N-alpha-glycoside linkage, was first synthesized by the coupling of triglycosyldipeptide active ester with the nonadecapeptide (3-21) using allyloxycarbonyl group as the final protecting group. A beta-anomeric glycopeptide was also prepared.

  DOI：

  10.1016/s0040-4039(00)74132-3
• 作为产物：
  描述：

  乙酸酐 、 异麦芽糖 在 吡啶 作用下， 生成 Isomaltose octaacetat
  参考文献：
  名称：

  Glycosylated tris-bipyridine ferrous complexes for probing a mechanism behind carbohydrate-carbohydrate interactions: Spatial carbohydrate packing of glycoclusters changes on additions of salts in carbohydrate- and anion-dependent manners

  摘要：

  2,2'-Bipyridines containing two beta-maltoside, beta-lactoside, or beta-isomaltoside appendages were prepared and successively complexed with ferrous ion to afford hexavalent glycoclusters having tris-bipyridine ferrous complex cores. Each of these metalloglycoclusters showed unique UV-vis and CD spectral changes upon addition of chloride, nitrate, and sulfate salts in carbohydrate- and anion-dependent manners. The results indicate that spatial carbohydrate packing of the metalloglycoclusters changes upon addition of these anions and that different anions stabilize different carbohydrate packings. Furthermore, the sulfates specifically enhance the rheological properties of aqueous solutions containing the metalloglycocluster containing beta-lactoside appendages. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2018.08.017

文献信息

• Stereoselective α-Glucosylation with Tetra-<i>O</i>-benzyl-α-D-glucose and a Mixture of Trimethylsilyl Bromide, Cobalt(II) Bromide, Tetrabutylammonium Bromide, and a Molecular Sieve. A Synthesis of 3,6-Di-<i>O</i>-(α-D-glucopyranosyl)-D-glucose
  作者：Shinkiti Koto、Naohiko Morishima、Chiharu Kusuhara、Shigeko Sekido、Toyosaku Yoshida、Shonosuke Zen

  DOI：10.1246/bcsj.55.2995

  日期：1982.9

  A mixture of trimethylsilyl bromide, cobalt(II) bromide, tetrabutylammonium bromide, and a molecular sieve (4A) is effective for the stereoselective, one-stage α-glucosylation of alcohol with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose in dichloromethane. Using this procedure, several disaccharide derivatives as well as O-α-D-glucopyranosyl-(1→3)]-O-[α-D-glucopyranosyl-(1→6)]-D-glucopyranose are synthesized

  三甲基溴化甲硅烷、溴化钴 (II)、溴化四丁基铵和分子筛 (4A) 的混合物可有效用于醇与 2,3,4,6-四-O-苄基的立体选择性、一步 α-葡萄糖基化-α-D-吡喃葡萄糖在二氯甲烷中。使用此程序，合成了几种二糖衍生物以及 O-α-D-吡喃葡萄糖基-(1→3)]-O-[α-D-吡喃葡萄糖基-(1→6)]-D-吡喃葡萄糖。
• Oxidation and degradation of maltose and isomaltose by persulfate
  作者：Yen-Yuan Chen、Ryuichi Oshima、Toshiyuki Uryu、Ju Kumanotani、Junichi Tsuchiya

  DOI：10.1016/s0008-6215(00)90757-2

  日期：1985.8

  Abstract Maltose and isomaltose were oxidized and degraded by ammonium persulfate in 66.7 mmol aqueous phosphate buffer (pH 7.1). Product and e.s.r. studies suggested that radicals formed by C-H abstraction at C-1 and C-4 were predominant for oxidation of maltose, whereas C-H abstraction of isomaltose proceeded preferentially at C-5 of the reducing glucose group.

  摘要在66.7 mmol pH 7.1的磷酸盐水溶液中，过硫酸铵将麦芽糖和异麦芽糖氧化并降解。乘积和esr研究表明，在C-1和C-4处通过CH提取形成的自由基是麦芽糖氧化的主要反应，而异麦芽糖的CH提取则优先在还原葡萄糖基团的C-5进行。
• An efficient and stereocontrolled synthesis of the nephritogenoside core structure
  作者：Makoto Sasaki、Kazuo Tachibana、Hiroshi Nakanishi

  DOI：10.1016/0040-4039(91)80430-e

  日期：1991.11

  An efficient and stereocontrolled synthesis of the core trisaccharide 2 of nephritogenic glycopeptide, nephritogenoside 1 is described. Key to our synthetic strategy was β-selective glycosylation without neighboring group participation.

  核心三糖的有效和立体控制合成2肾炎糖肽，nephritogenoside 1进行说明。我们合成策略的关键是没有相邻基团参与的β-选择性糖基化。
• Synthesis of sterically crowded derivatives of anomeric pairs of d-glucose disaccharides
  作者：Sanford Mendonca、Roger A. Laine

  DOI：10.1016/j.carres.2005.05.016

  日期：2005.9

  Derivatization of carbohydrates is of considerable interest since the derivatives can be used for structural studies in the field of mass spectrometry. We report here the synthesis of a series of sterically crowded derivatives of various linkage and stereo-isomeric glucose-glucose disaccharides with the impetus being to understand the effect of these derivatized groups on fragmentation of the glycosidic

  碳水化合物的衍生化具有相当大的意义，因为该衍生物可用于质谱领域的结构研究。我们在这里报告了一系列各种键和立体异构体葡萄糖-葡萄糖二糖的空间拥挤衍生物的合成，其推动力是了解这些衍生基团对糖苷键断裂的影响以及用于识别糖基键的方法的发展。异头配置。已经合成了全烷基化的（甲基，乙基，丙基，丁基和戊基），过酸酯化的（乙酰基，新戊酰基，甲基磺酰基）和全甲硅烷基化的（叔丁基-二甲基甲硅烷基）葡萄糖-葡萄糖二糖衍生物。报告。
• Synthesis of 5-O-oligoglucosyl extended α-(2→4)-Kdo disaccharides corresponding to inner core fragments of Moraxellaceae lipopolysaccharides
  作者：Barbara Pokorny、Paul Kosma

  DOI：10.1016/j.carres.2015.12.009

  日期：2016.3

  The heptose-deficient inner core of the lipopolysaccharide of several pathogenic strains of the Moraxellaceae family (Moraxella, Acinetobacter) and of Bartonella henselae, respectively, comprises an α-D-glucopyranose attached to position 5 of Kdo. In continuation of the synthesis of fragments of Acinetobacter haemolyticus LPS, the branched α-Glcp-(1 → 5)[α-Kdo-(2 → 4)]-α-Kdo trisaccharide motif was

  莫拉氏菌科（Moraxella，不动杆菌）和汉氏巴尔通体的数种致病菌株的脂多糖的庚糖缺陷的内核分别包含附着于Kdo 5位的α-D-吡喃葡萄糖。为了继续合成溶血不动杆菌LPS的片段，精心设计了分支的α-Glcp-（1→5）[α-Kdo-（2→4）]-α-Kdo三糖基序。使用4,6-O-亚苄基N-苯基三氟乙酰亚氨基葡糖基供体，可以高收率和公平的端基选择性实现适当保护的，α-（2→4）交联的Kdo-二糖的糖基化作用。随后的区域选择性还原性亚苄基打开提供了三糖受体，其被β-D-吡喃葡萄糖基和异麦芽糖基残基所扩展。