ethyl 3,4-O-isopropylidene-6-O-tert-butyldimethylsilyl-1-thio-β-D-galactopyranoside | 172146-96-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3,4-O-isopropylidene-6-O-tert-butyldimethylsilyl-1-thio-β-D-galactopyranoside
• 英文别名: ethyl 6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside；ethyl 6-O-tert-butyldimethylsilyl-3,4-isopropylidene-1-thio-β-D-galactopyranoside；ethyl 6-O-t-butyldimethylsilyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside；(3aS,4R,6S,7R,7aR)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-ethylsulfanyl-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 172146-96-2
• 化学式: C₁₇H₃₄O₅SSi
• 分子量: 378.605
• InChiKey: JDIZTNBFIOHYSJ-QMIVOQANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 3,4-O-isopropylidene-6-O-tert-butyldimethylsilyl-1-thio-β-D-galactopyranoside 在 lithium aluminium tetrahydride 、 2,6-二叔丁基-4-甲基吡啶 、 硫化氢 、 sodium hydride 、 三乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 (2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[2-O-(3,3-di-tert-butyloxycarbonylpropyl)-3,4-O-isopropylidene-6-O-tert-butyldimethylsilyl-α-D-galactopyranosyloxy]-4-octadecene
  参考文献：
  名称：

  Novel mimics of sialyl Lewis X

  摘要：

  A series of potent inhibitors of P-selectin as potential anti-inflammatory agents is reported. These compounds are derivatives of galactocerebrosides bearing a malonate side chain in positions 2 and 3 of the galactose moiety. Based on the binding mode of sialyl Lewis X, the two acidic groups of the malonate are designed to form ionic interactions with two important lysines in the active site of P-selectin, Lys113 and Lys111. On the other hand, the 4- and 6-hydroxy groups on the galactose ring are arranged to chelate the calcium ion in the P-selectin active site. The synthesis and the biological activity of this series of compounds are described. Lead compounds having a greater potency than sialyl Lewis X are identified. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00015-3
• 作为产物：
  描述：

  1-硫代-Β-D-乙基半乳糖苷 在 4-二甲氨基吡啶 、 对甲苯磺酸 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 2.0h， 生成 ethyl 3,4-O-isopropylidene-6-O-tert-butyldimethylsilyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Oligosaccharide recognition by antibodies: Synthesis and evaluation of talose oligosaccharide analogues

  摘要：

  一系列单糖（4-6）、二糖（3、7-12）和三糖（13-15）类似物已经合成，它们是原生配体2的类似物，填充了单克隆抗体Se 155.4的结合位点，并通过固相和溶液相测定了它们的生物活性。二糖类似物的合成旨在将半乳糖替换为甘露糖的O-2位置的各种烷基。其中一种O-2烷基类似物的活性为观察到的三糖活性的75%，表明溶剂暴露的半乳糖残基与抗体结合位点之间只有弱的净键合。通过将原生配体2的甘露糖残基替换为甜菜糖合成了甜菜糖类似物13和14，这些配体的活性为原生配体2的三分之一到一半。这些活性变化与甜菜糖破坏溶剂水的能力之间没有明显的相关性。关键词：阿贝酮，3,6-二去氧-D-木糖-己糖，甜菜糖二糖和三糖，抗体寡糖相互作用，碳水化合物的分子识别，抗体复合物中的水，沙门氏菌LPS，单克隆抗体Se 155.4，细菌O抗原。

  DOI：

  10.1139/v02-118

文献信息

• Sulfated .alpha.-glycolipid derivatives as cell adhesion inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US05663151A1

  公开（公告）日：1997-09-02

  There is provided novel sulfated .alpha.-glycolipid compounds of the formula ##STR1## wherein R is an acyl residue of a fatty acid; R.sup.1 is --(CH.dbd.CH).sub.m --(CH.sub.2).sub.n --CH.sub.3 ; R.sup.2, R.sup.3, R.sup.4 and R.sup.6 are independently at least two --SO.sub.3 H; R.sup.2, R.sup.3, R.sup.4 R.sup.5 and R.sup.6 each are independently hydrogen, unsubstituted or substituted alkanoyl, arylalkyl or arylcarbonyl wherein said substituent is selected from halogen, C.sub.1-4 alkyl, trifluoromethyl, hydroxy and C.sub.1-4 alkoxy; m is an integer of 0 or 1; n is an integer of from 5 to 14, inclusive; or a non-toxic pharmaceutically acceptable salt, solvate or hydrate thereof which are inhibitors of selectin-mediated cellular adhesion and are useful in the treatment or prevention of inflammatory diseases and other pathological conditions in mammals.

  提供了一种新型的磺酸化α-糖脂化合物，其化学式为##STR1##其中R是脂肪酸的酰基残基；R.sup.1是--(CH.dbd.CH).sub.m--(CH.sub.2).sub.n--CH.sub.3；R.sup.2、R.sup.3、R.sup.4和R.sup.6独立地至少有两个--SO.sub.3 H；R.sup.2、R.sup.3、R.sup.4、R.sup.5和R.sup.6各自独立地是氢、未取代或取代的烷酰基、芳基烷基或芳基羰基，其中所述取代基选自卤素、C.sub.1-4烷基、三氟甲基、羟基和C.sub.1-4烷氧基；m是0或1的整数；n是从5到14的整数，包括在内；或其非毒性药学上可接受的盐、溶剂化合物或水合物，它们是选择素介导的细胞粘附的抑制剂，并且在哺乳动物的炎症性疾病和其他病理条件的治疗或预防中是有用的。
• Synthesis of the tetrasaccharide repeating unit of the cryoprotectant capsular polysaccharide from <i>Colwellia psychrerythraea</i> 34H
  作者：Giulia Vessella、Angela Casillo、Antonio Fabozzi、Serena Traboni、Alfonso Iadonisi、Maria Michela Corsaro、Emiliano Bedini

  DOI：10.1039/c9ob00104b

  日期：——

  unique capsular polysaccharide (CPS) with anti-freeze properties similar to those of the well-known anti-freeze (glyco)proteins. The tetrasaccharide repeating unit of the CPS – constituted of alternating amino sugars and uronic acid moieties in a glycosaminoglycan-like fashion with an amide-linked threonine (Thr) decoration – was synthesized as an O-n-propyl glycoside. The synthesis faced some challenging

  Colwellia psychrerythraea 34H是一种嗜冷革兰氏阴性细菌，能够通过产生独特的荚膜多糖（CPS）而在零下温度下存活，该荚膜多糖具有与众所周知的抗冻（glyco）蛋白相似的抗冻特性。合成了CPS的四糖重复单元，它是由交替的氨基糖和糖醛酸部分组成，呈类似糖胺聚糖的形式，带有酰胺连接的苏氨酸（Thr）装饰物，被合成为O-正丙基糖苷。合成面临一些挑战性的特征，例如建立拥挤的[→2）α- D -Gal p（1→]部分以及两个尿嘧啶单元仅用于在其中一个区域选择性插入Thr酰胺，得到的四糖的NMR数据证实了拟南芥（C. psychrerythraeaea）多糖的结构。
• [EN] SYNTHETIC VACCINES AGAINST STREPTOCOCCUS PNEUMONIAE TYPE 1<br/>[FR] VACCINS SYNTHÉTIQUES CONTRE LE STREPTOCOCCUS PNEUMONIAE DE TYPE 1
  申请人：MAX PLANCK GES ZUR FÖRDERUNG DER WISSENSCHAFTEN E V

  公开号：WO2015004041A1

  公开（公告）日：2015-01-15

  The present invention relates to the total synthesis of saccharide structures contained in the capsular polysaccharide of Streptococcus pneumoniae type 1, to glycoconjugates containing said saccharide structures obtained by total synthesis and to use of such glycoconjugates and pharmaceutical compositions thereof in the immunization against diseases associated with bacteria containing said saccharide structures in their capsular polysaccharide, and more specifically associated with Streptococcus pneumoniae.

  本发明涉及肺炎链球菌1型胶囊多糖中含有的糖结构的全合成，涉及通过全合成获得含有该糖结构的糖蛋白共轭物，以及利用这种糖蛋白共轭物和制药组合物在免疫过程中用于预防与其胶囊多糖中含有该糖结构的细菌相关的疾病，更具体地与肺炎链球菌相关。
• Synthetic vaccines against Streptococcus pneumoniae
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP2845860A1

  公开（公告）日：2015-03-11

  The present invention relates to the total synthesis of saccharide structures contained in the capsular polysaccharide of Streptococcus pneumoniae type 1, to glycoconjugates containing said saccharide structures obtained by total synthesis and to use of such glycoconjugates and pharmaceutical compositions thereof in the immunization against diseases associated with bacteria containing said saccharide structures in their capsular polysaccharide, and more specifically associated with Streptococcus pneumoniae.

  本发明涉及对肺炎链球菌1型胶囊多糖中含有的糖结构进行全合成，以及通过全合成获得含有该糖结构的糖蛋白结合物，以及利用这种糖蛋白结合物和其制剂在免疫接种中用于预防与含有这种糖结构的细菌相关的疾病，更具体地与肺炎链球菌相关。
• Development of Fully and Partially Protected Fucosyl Donors for Oligosaccharide Synthesis
  作者：Robin Daly、Thomas McCabe、Eoin M. Scanlan

  DOI：10.1021/jo302487c

  日期：2013.2.1

  and the silyl protecting groups could be removed in the presence of unsaturated bonds. The disilyl-protected donor was found to behave as an efficient, partially protected glycosyl donor. The synthetic scope and limitations of these new donors is presented. Both donors were applied to the synthesis of a Lewis X trisaccharide displaying a propargyl group at the anomeric position. It was determined that

  完全和部分终止使用描述了丁基丁基二甲基甲硅烷基（TBDMS）保护的岩藻糖硫糖苷作为寡糖合成的糖基供体。制备了三甲硅烷基和二甲硅烷基保护的硫代糖苷供体，并研究了它们在一系列活化条件下的反应性。发现两个甲硅烷基保护的供体均提供所需α产物的良好产率，并且可以在不饱和键存在下除去甲硅烷基保护基。发现二甲硅烷基保护的供体表现为有效的，部分保护的糖基供体。介绍了这些新捐助者的综合范围和局限性。将两个供体均用于在异头位置显示炔丙基的Lewis X三糖的合成。