2,3:5,6-Di-O-isopropylidene-4-O-(3',4'-O-isopropylidene-6'-O-(1-methyloxy-1-methylethyl)-β-D-galactopyranosyl)-aldehydo-D-glucose dimethyl acetal | 102674-58-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 2,3:5,6-Di-O-isopropylidene-4-O-(3',4'-O-isopropylidene-6'-O-(1-methyloxy-1-methylethyl)-β-D-galactopyranosyl)-aldehydo-D-glucose dimethyl acetal
• 英文别名: 4-O-[6-O-(1-methoxy-1-methylethyl)-3,4-O-isopropylidene-β-D-galactopyranosyl]-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal；(3aS,4R,6S,7R,7aR)-6-[(R)-[(4S,5R)-5-(dimethoxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-4-(2-methoxypropan-2-yloxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 102674-58-8
• 化学式: C₂₇H₄₈O₁₃
• 分子量: 580.67
• InChiKey: CIHHWOKEARRSRQ-ZQNATQRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2,3:5,6-Di-O-isopropylidene-4-O-(3',4'-O-isopropylidene-6'-O-(1-methyloxy-1-methylethyl)-β-D-galactopyranosyl)-aldehydo-D-glucose dimethyl acetal 在 甲醇 作用下， 生成 4-O-(3,4-isopropylidene-β-D-galactopyranosyl)-2,3:5,6-bis-O-isopropylidene-D-glucose dimethyl acetal
  参考文献：
  名称：

  Synthesis of Disaccharides, Containing Sulfur in the Ring of the Reducing Monosaccharide Unit, Through a Nonglycosylating Chemical Strategy

  摘要：

  DOI：

  10.1002/(sici)1521-3765(19990503)5:5<1512::aid-chem1512>3.0.co;2-a
• 作为产物：
  描述：

  2,2-二甲氧基丙烷 、 β-乳糖 在 对甲苯磺酸 作用下， 反应 5.0h， 生成 4-O-(3,4-isopropylidene-β-D-galactopyranosyl)-2,3:5,6-bis-O-isopropylidene-D-glucose dimethyl acetal 、 2,3:5,6-Di-O-isopropylidene-4-O-(3',4'-O-isopropylidene-6'-O-(1-methyloxy-1-methylethyl)-β-D-galactopyranosyl)-aldehydo-D-glucose dimethyl acetal
  参考文献：
  名称：

  Disperse dyes soluble in water

  摘要：

  该应用描述了一种水溶性分散染料的一般化学式(I) D-L-Sn (I) 其中： D是一种不溶于水的分散染料 L是一个连接物 S是一种糖 n的取值范围在2到4之间 这些染料能够以均匀的方式染色天然纤维和纺织品，还能够染色包括不同纤维的纺织材料，并且通过微生物的消化具有高生物降解性，这些微生物在分子中找到了有用的营养以供其生存和繁殖；还描述了上述染料的制备过程及其用途。

  公开号：

  EP2085434A1

文献信息

• Synthesis and structure–activity relationships of di- and trisaccharide inhibitors for Shiga-like toxin Type 1
  作者：Pavel I. Kitov、David R. Bundle

  DOI：10.1039/b009685g

  日期：——

  The syntheses of galabiose and Pk-trisaccharide analogues in which selected hydroxy groups are replaced by O-methyl, amino deoxy, acetamido deoxy, and carboxyalkyl groups are reported. The ability of these inhibitors to block E. coli verotoxin 1 binding to its mammalian cell-surface receptor are evaluated by a solid-phase competition assay. The synthesis of a biotinylated glycoconjugate for this assay

  合成的半乳糖和P k-三糖类似物，其中选定的羟基被O-甲基取代，氨基 脱氧 乙酰氨基报道了脱氧和羧基烷基。这些的能力抑制剂通过固相竞争测定法评估阻断大肠杆菌维毒素1与其哺乳动物细胞表面受体的结合的方法。描述了用于该测定法的生物素化的糖缀合物的合成，其中构建了P k-三糖系链衍生物70并将其共价附接到牛血清白蛋白上，随后是生物素化。半乳糖衍生物4和5含有羧甲基β-半乳糖残基的O --2处的羧基或羧基乙基取代基显示出15-20倍的活性增加甲基糖苷半乳糖。对于相应的羧甲基取代的P k-三糖类似物13，未观察到这种增强的活性。通过与P k-三糖类似物复合的Verotoxin 1的晶体结构合理化抑制数据，并为二聚体的设计提供了见识抑制剂可以利用毒素B亚基的独特结合位点分布。该讨论提供了由有序人扮演的重要角色的另一个示例。水 糖中的分子蛋白质 复合体。
• Synthesis of Water-Soluble Large Naturalised Dyes Through Double Glycoconjugation
  作者：Jalal Isaad、Massimo Rolla、Roberto Bianchini

  DOI：10.1002/ejoc.200801302

  日期：2009.6

  Recently we started to develop a new class of dyes based upon the glycoconjugation of disperse dyes with mono- or disaccharides. We used the term “naturalised” to describe these dyes because we used natural lactose in the glycoconjugation process, and also because they are similar to real natural dyes, the hydrosolubility of which is based upon the saccharidic moiety attached to the chromophore, as

  最近，我们开始开发一类基于分散染料与单糖或二糖的糖共轭的新型染料。我们使用术语“天然化”来描述这些染料，因为我们在糖缀合过程中使用了天然乳糖，还因为它们类似于真正的天然染料，其水溶性基于附着在发色团上的糖基部分，如胭脂虫红酸或红花素。提交归化过程的合成染料由小的发色团分子组成，主要是偶氮，而当通过二价间隔物添加单个乳糖分子时，具有较高质量的较大染料分子在水中没有明显的溶解度，这与较小的染料。为了克服这个困难，在本文中，我们提出了通过双糖缀合过程插入两个乳糖单元的第一种方法。这里介绍的程序允许成功插入一个间隔物，丙二酸，它可以与两个乳糖单元连接，以便即使是大染料也能溶解。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009 )
• Ethereal Glycoconjugated Azodyes (GADs): A New Group of Water-Soluble, Naturalised Dyes
  作者：Roberto Bianchini、Giorgio Catelani、Riccardo Cecconi、Felicia D'Andrea、Lorenzo Guazzelli、Jalal Isaad、Massimo Rolla

  DOI：10.1002/ejoc.200700632

  日期：2008.1

  deals with azodyes naturalised through glycoconjugation with a very common saccharide – lactose – and with its galactose and glucose components. The conjugation takes place through a bifunctional linker, here a terminal dibromoalkane, so the final products are very stable diether derivatives of the starting dyes. These transformations produce naturalised dyes – indeed, water-soluble and multipurpose

  本报告涉及通过与一种非常常见的糖类——乳糖——及其半乳糖和葡萄糖成分进行糖结合而归化的偶氮染料。结合通过双功能接头进行，此处为末端二溴烷烃，因此最终产物是起始染料的非常稳定的二醚衍生物。这些转化产生了自然化染料——实际上是水溶性和多用途的——能够在不添加化学添加剂（如表面剂）的情况下对不同的材料进行染色。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2008 年）
• Synthesis of 5-Thio-<scp>l</scp>-fucose-Containing Disaccharides, as Sequence-Specific Inhibitors, and 2‘-Fucosyllactose, as a Substrate of α-<scp>l</scp>-Fucosidases
  作者：Masayuki Izumi、Osamu Tsuruta、Satoru Harayama、Hironobu Hashimoto

  DOI：10.1021/jo961725h

  日期：1997.2.1

  Four 5-thio-L-fucose-containing disaccharides having alpha(1-->6), alpha(1-->3), alpha(1-->4)GlcNAc, and alpha(1-->2-Gal linkages (compounds 1-4, respectively) were synthesized as potential alpha-L-fucosidase inhibitors. The glycosylation reactions using 2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl trichloroacetimidate as a glycosyl donor and BF3 . OEt(2) as a catalyst gave mainly alpha-linked disaccharides. Only alpha(1-->2)-linked disaccharide 4 showed inhibitory activity (K-i = 0.21 mM) against Bacillus alpha-L-fucosidase which hydrolyzes the Fuc alpha(1-->2) linkage specifically. The results suggested that sequence specificity of an enzyme could be estimated from the inhibitory activities of the compounds 1-4. In contrast, every disaccharide showed inhibitory activity (K-i = 30-91 mu M) against bovine epididymis alpha-L-fucosidase.
• Disperse dyes soluble in water
  申请人：Universita' Degli Studi di Firenze

  公开号：EP2085434A1

  公开（公告）日：2009-08-05

  The Application describes disperse dyes soluble in water of general formula (I)         D-L-Sn     (I) wherein: D is a disperse dye insoluble in water L is a linker S is a sugar n is comprised between 2 and 4 that are able to dye in an homogeneous way natural fibres and textiles and also textile materials including different fibres, and have high biodegradability through digestion by micro organisms, that found in the molecule itself a useful nourishment for their survival and proliferation; processes for the preparation of the above said dyes and their use are also described.

  该应用描述了一种水溶性分散染料的一般化学式(I) D-L-Sn (I) 其中： D是一种不溶于水的分散染料 L是一个连接物 S是一种糖 n的取值范围在2到4之间 这些染料能够以均匀的方式染色天然纤维和纺织品，还能够染色包括不同纤维的纺织材料，并且通过微生物的消化具有高生物降解性，这些微生物在分子中找到了有用的营养以供其生存和繁殖；还描述了上述染料的制备过程及其用途。