(2,3-di-O-acetyl)hexakis(2,3,6-tri-O-acetyl)cyclomaltoheptaose | 116531-20-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3-di-O-acetyl)hexakis(2,3,6-tri-O-acetyl)cyclomaltoheptaose
• 英文别名: [(1R,3R,5R,6R,8R,10R,11R,13R,15R,16R,18R,20R,21R,23R,25R,26R,28R,30R,31R,33R,35R,36S,37R,38S,39R,40S,41R,42S,43R,44S,45R,46S,47R,48S,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecaacetyloxy-15,20,25,30,35-pentakis(acetyloxymethyl)-10-(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-5-yl]methyl acetate
• CAS: 116531-20-5
• 化学式: C₈₂H₁₁₀O₅₅
• 分子量: 1975.74
• InChiKey: IGAFQALRWXLZGJ-IAZZLGEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  137
• 可旋转键数：
  47
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  675
• 氢给体数：
  1
• 氢受体数：
  55

反应信息

• 作为反应物：
  描述：

  (2,3-di-O-acetyl)hexakis(2,3,6-tri-O-acetyl)cyclomaltoheptaose 在 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以89%的产率得到(2,3-di-O-acetyl-6-deoxy-6-fluoro)hexakis(2,3,6-tri-O-acetyl)cyclomaltoheptaose
  参考文献：
  名称：

  Synthesis and Drug Complexation Studies with β-Cyclodextrins Fluorinated on the Primary Face

  摘要：

  Three fluorinated beta-cyclodextrin derivatives, namely 5, 9 and 12, were prepared with the hope that the fluorine reporter group may assist in direct evaluation of the complexation properties of these potential drug carriers. Two of the synthesized derivatives, the previously reported monofluoro-beta-cyclodextrin 9 and the novel trifluoroethylthio-beta-cyclodextrin 12, displayed reasonable aqueous solubility and thus were suitable for drug-cyclodextrin complexation studies. Preliminary NMR results (H-1 and F-19) on the host-guest complex formation of both of these cyclodextrin derivatives with amantidine, a therapeutic agent employed in the treatment of Influenza A infections, are also presented.

  DOI：

  10.1080/07328309908543991
• 作为产物：
  描述：

  (2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl)hexakis(2,3,6-tri-O-acetyl)cyclomaltoheptaose 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 1.5h， 以57.2%的产率得到(2,3-di-O-acetyl)hexakis(2,3,6-tri-O-acetyl)cyclomaltoheptaose
  参考文献：
  名称：

  6-O-α-d-吡喃葡萄糖基环麦芽庚糖的合成

  摘要：

  摘要通过将环麦芽庚糖与叔丁基二甲基甲硅烷基氯在吡啶中反应，然后进行乙酰化和去甲硅烷基化反应，制得（2,3-二-O-乙酰基）六（2,3,6-三-O-乙酰基）环麦芽九糖。使用三氟甲磺酸作为催化剂，用2,3,4,6-四-O-苄基-1-O-三氯乙酰亚胺基-α-d-吡喃葡萄糖进行糖基化，然后从产物中除去保护基，得到标题化合物。

  DOI：

  10.1016/0008-6215(88)84140-5

文献信息

• A Convenient Synthesis of<i>S</i>-(α-D- and<i>S</i>-(β-D)-Glucopyranosyl-6-thiomaltodextrins
  作者：Sylvain Cottaz、Hugues Driguez

  DOI：10.1055/s-1989-27384

  日期：——

  (2,3-Di-O-acetyl-6-deoxy-6-iodo)-hexakis(2,3,6-tri-O-acetyl) cyclomaltoheptaose (9) was prepared by reaction of cyclomaltoheptaose (5) with trityl chloride followed by acetylation, O-detritylation, mesylation, and displacement of the mesyloxy group by iodine using sodium iodide. This cyclomaltoheptaose derivative was S-glycosylated in high yield with either of the anomers of 2,3,4,6-tetra-O-acetyl-S-acetyl-1-thioglucopyranose (1α or 1β). Deacetylation afforded S-(α -D- and S-(α-D-glucopyranosyl)-6-thiocyclomaltoheptaose (10b) and 11b, respectively. Procedures arising from model experiments also provided a new syntheses of S-(α-D-glucopyranosyl)-6-thiomaltose (3b) and of its β-isomer (4b).

  通过环麦芽庚糖（5）与三苯甲基氯反应，随后进行乙酰化、脱三苯甲基、甲磺酰化和碘离子置换甲磺酰基，制备了（2,3-二-O-乙酰基-6-脱氧-6-碘）-海克西（2,3,6-三-O-乙酰基）环麦芽庚糖（9）。该环麦芽庚糖衍生物在高产率条件下与2,3,4,6-四-O-乙酰基-S-乙酰基-1-硫代葡萄糖吡喃糖（1α或1β）中的任一种非对映异构体进行S-糖苷化反应。脱乙酰化得到S-(α-D-葡萄糖吡喃糖)-6-硫代环麦芽庚糖（10b）和11b。从模型实验中得出的方法还提供了S-(α-D-葡萄糖吡喃糖)-6-硫代麦芽糖（3b）及其β-异构体（4b）的新合成方法。
• Characterization of five isomers of branched cyclomaltoheptaose (β CD) having degree of polymerization (d.p.) = 9: Reinvestigation of three positional isomers of diglucosyl-β CD
  作者：Kyoko Koizumi、Toshiko Tanimoto (née Utamura)、Yasuyo Okada、Noriko Nakanishi、Nagako Kato、Yosuke Tagaki、Hitoshi Hashimoto

  DOI：10.1016/0008-6215(91)84013-5

  日期：1991.8

  has been newly isolated from a glucosyl-beta CD mixture prepared by hydrolysis with glucoamylase of a maltosyl-beta CD mixture, synthesized from maltose and beta CD through the reverse action of pullulanase. Chromatographic behavior and spectral data (13C-n.m.r. and f.a.b.-m.s.) of these isomers of branched beta CD (1-4), as well as those of another isomer prepared by the reverse action of hydrolytic

  通过甲基化分析和化学合成已证实，从带有大芽孢杆菌环麦芽糖糊精葡聚糖转移酶的大规模制备β-CD的母液中分离出的支链环麦芽七糖（βCD）的三个异构体是6（1），6（4）-二-O-（α-D-吡喃葡萄糖基）-环麦芽庚糖（1），6（1），6（3）-二-O-（α-D-吡喃葡萄糖基）-环麦芽庚糖（2）和6-O- α-异麦芽糖基）-环麦芽庚糖（4）代替了6（1），6（2）-二-O-（α-D-吡喃葡萄糖基）-麦芽七糖（3），这在先前的论文中被错误地描述了。已经从通过用葡糖淀粉酶的逆作用由麦芽糖和βCD合成的麦芽糖β-CD混合物的葡糖淀粉酶水解制备的葡糖基-βCD混合物中新分离了化合物3。色谱行为和光谱数据（13C-nmr和fa
• COTTAZ, SYLVAIN;DRIGUEZ, HUGUES, SYNTHESIS,(1989) N0, C. 755-759
  作者：COTTAZ, SYLVAIN、DRIGUEZ, HUGUES

  DOI：——

  日期：——
• FUGEDI, PETER;NANASI, PAL;SZEJTLI, JOZSEF, CARBOHYDR. RES., 175,(1988) N 2, 173-181
  作者：FUGEDI, PETER、NANASI, PAL、SZEJTLI, JOZSEF

  DOI：——

  日期：——