O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-2)-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-(1-4)-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal | 77668-00-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-2)-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-(1-4)-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal
• 英文别名: O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1→2)-O-(3,4-isopropylidene-β-D-galactopyranosyl)-(1→4)-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal；O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(l→2)-O-(3,4-isopropylidene-β-D-galacto-pyranosyl)-(l→4)-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal；[(3aS,4R,6S,7R,7aS)-6-[(R)-[(4S,5R)-5-(dimethoxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-2,2-dimethyl-7-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methanol
• CAS: 77668-00-9
• 化学式: C₅₀H₆₈O₁₆
• 分子量: 925.08
• InChiKey: HFUCQTHXZDXGQE-MCCJOWEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  66
• 可旋转键数：
  19
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  159
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-2)-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-(1-4)-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal 在 水 、 碳酸氢铵 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  [EN] MULTIVALENT OLIGOSACCHARIDES
  [FR] OLIGOSACCHARIDES MULTIVALENTS

  摘要：

  幽门螺杆菌感染全球超过一半的人口，被认为是慢性胃炎、消化性溃疡和胃癌的主要原因之一。弯曲菌属是另一种肠道和胃部细菌，是细菌性腹泻最常见的原因。这两种微生物通过与上皮细胞表达的血型抗原相关或其他碳水化合物结合，附着在粘膜上。母乳喂养可以保护婴儿免受这些细菌感染，这是因为人乳中存在大量抗原寡糖。多价寡糖通过设计刚性和灵活的支架合成，以多样化呈现碳水化合物。这些化合物在纯化的鸡大肠粘膜上进行评估，其中一些化合物可以抑制细菌与粘膜的结合。这些多价寡糖是胃肠道疾病的有希望的预防和治疗抗菌剂。

  公开号：

  WO2013004669A1
• 作为产物：
  描述：

  4-O-(3,4-isopropylidene-β-D-galactopyranosyl)-2,3:5,6-bis-O-isopropylidene-D-glucose dimethyl acetal 在 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-2)-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-(1-4)-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal
  参考文献：
  名称：

  O-α-1-呋喃果糖基-（1→2）-O-β-d-吡喃半乳糖基-（1→4）-d-吡喃葡萄糖（2'-O-α-1-1-呋喃果糖基-乳糖）的合成

  摘要：

  摘要在二氯甲烷中用苯甲酰氯对2,3：5,6：3'，4'-三-O-异丙基半乳糖二甲基乙缩醛（1）进行选择性苯甲酰化，得到6'-O-苯甲酰衍生物（2）。从其nmr光谱推断出2的组成，并通过甲基化并随后水解为2-O-甲基-d-半乳糖和d-葡萄糖来证实。用2,3,4-三-O-苄基-α-1-呋喃果糖基溴化物对2进行糖苷化（由溴离子催化），得到2'-O连接的，完全保护的三糖（9）。9的O-脱苯甲酰化，然后进行脱缩醛化，得到三-O-苄基三糖（11）。随后11的苄基的氢解得到标题三糖。缩醛1被转化为单乙酸酯和二苯甲酸酯，并且还描述了从1开始的2'-O-甲基-乳糖的简单合成。

  DOI：

  10.1016/s0008-6215(00)84600-5

文献信息

• Bi- to tetravalent glycoclusters: synthesis, structure–activity profiles as lectin inhibitors and impact of combining both valency and headgroup tailoring on selectivity
  作者：Guan-Nan Wang、Sabine André、Hans-Joachim Gabius、Paul V. Murphy

  DOI：10.1039/c2ob25870f

  日期：——

  The emerging functional versatility of cellular glycans makes research on the design of synthetic inhibitors a timely topic. In detail, the combination of ligand (or headgroup or contact site) structure with spatial parameters that depend on topological and geometrical factors underlies the physiological selectivity of glycan-protein (lectin) recognition. We herein tested a panel of bi-, tri- and tetravalent compounds against two plant agglutinins and adhesion/growth-regulatory lectins (galectins). In addition, we examined the impact of headgroup tailoring (converting lactose to 2′-fucosyllactose) in combination with valency increase in two assay types of increasing biorelevance (from solid-phase binding to cell binding). Compounds were prepared using copper-catalysed azide alkyne cycloaddition from peracetylated lactosyl or 2′-fucosyllactosyl azides. Significant inhibition was achieved for the plant toxin with a tetravalent compound. Different levels of sensitivity were noted for the three groups of the galectin family. The headgroup extension to 2′-fucosyllactose led to a selectivity gain, especially for the chimera-type galectin-3. Valency increase established discrimination against the homodimeric proteins, whereas the combination of valency with the headgroup extension led to discrimination against the tandem-repeat-type galectin-8 for chicken galectins but not human galectins-3 and -4. Thus, detailed structure–activity profiling of glycoclusters combined with suitably modifying the contact site for the targeted lectin will help minimize cross-reactivity among this class of closely related proteins.

  细胞糖类日益显现的功能多样性使得合成抑制剂设计的研究成为一个及时的话题。具体而言，配体（或头基或接触位点）结构与依赖于拓扑和几何因素的空间参数的结合构成了糖类-蛋白质（凝集素）识别的生理选择性。本文测试了一系列二价、三价和四价化合物，以针对两种植物凝集素和粘附/生长调节凝集素（伽星素）。此外，我们还研究了头基调节（将乳糖转化为2'-呋喃乳糖）与在两个生物相关性的测定类型中增加价态的结合影响（从固相结合到细胞结合）。化合物通过铜催化的叠氮炔烃环加成反应，从过乙酰化的乳糖基或2'-呋喃乳糖基叠氮化物制备而成。使用四价化合物对植物毒素实现了显著的抑制。伽星素家族的三个组别表现出不同程度的敏感性。将头基延伸至2'-呋喃乳糖带来了选择性增强，特别是对于混合型伽星素-3。增加价态在区分同源二聚体蛋白方面表现出作用，而将价态与头基延伸结合则导致对鸡伽星素的串联重复型伽星素-8的区分，但对人类伽星素-3和-4则没有影响。因此，详细的糖簇结构-活性谱分析结合适当地调节目标凝集素的接触位点，将有助于最小化这一类密切相关蛋白之间的交叉反应性。
• METHOD FOR THE SYNTHESIS OF A TRISACCHARIDE
  申请人：Dékany Gyula

  公开号：US20130131334A1

  公开（公告）日：2013-05-23

  The present invention relates to an improved synthesis of a trisaccharide of the formula (1), novel intermediates used in the synthesis and the preparation of the intermediates.

  本发明涉及一种改进的合成方法，用于合成式（1）的三糖，以及在合成过程中使用的新型中间体和中间体的制备。
• [EN] SYNTHESIS OF 2'-O-FUCOSYLLACTOSE<br/>[FR] SYNTHÈSE DE 2'-O-FUCOSYLLACTOSE
  申请人：GLYCOM AS

  公开号：WO2010115934A1

  公开（公告）日：2010-10-14

  The present invention relates to an improved synthesis of a trisaccharide of the formula (1), novel intermediates used in the synthesis and the preparation of the intermediates.

  本发明涉及改进的三糖的合成方法，所述三糖的化学式为（1），以及合成过程中使用的新型中间体和中间体的制备。
• PROCESS FOR PRODUCING 2'-O-FUCOSYLLACTOSE
  申请人：BASF SE

  公开号：US20210130384A1

  公开（公告）日：2021-05-06

  The present invention relates to a method for preparing 2′-O-fucosyllactose, the intermediates obtainable by this method and the use of these intermediates. The preparation comprises the reaction of a protected fucose of the general formula (I) with a tri(C 1 -C 6 -alkyl)silyl iodide to give a protected 1-iodofucose followed by the reaction of the protected 1-iodofucose with a compound of the general formula (II), in the presence of at least one base and deprotecting the resulting coupling product to afford 2′-O-fucosyllactose. In this context, the variables are each defined as follows: R a and R b are the same or different and are —C(═O)—C 1 -C 6 -alkyl, or —C(═O)-phenyl, wherein said phenyl is unsubstituted or optionally has 1 to 5 substituents, or R a and R b together are a radical —(C═O)— or a substituted methylene radical —C(R d R e )—, R c is a radical R Si or is benzyl, wherein said benzyl is unsubstituted or optionally has 1, 2 or 3 substituents, R Si is a radical of the formula SiR f R g R h , where R f , R g and R h are the same or different and are C 1 -C 8 -alkyl for example, R 1 is a radical —C(═O)—R 11 or a radical SiR 12 R 13 R 14 R 2 are the same or different and are C 1 -C 8 -alkyl for example; R 3 are the same or different and are for example C 1 -C 8 -alkyl or both radicals R 3 together form a linear C 1 -C 4 -alkenyl, which is unsubstituted or has 1 to 6 methyl groups as substituents.

  本发明涉及一种制备2'-O-岩藻糖乳的方法，以及通过该方法可获得的中间体和这些中间体的用途。该制备包括将一般式（I）的保护岩藻糖与三（C1-C6-烷基）硅基碘反应，得到保护1-碘岩藻糖，然后将保护1-碘岩藻糖与一般式（II）的化合物在至少一种碱的存在下反应，并去保护所得的偶联产物以得到2'-O-岩藻糖。在这种情况下，变量的定义如下：Ra和Rb相同或不同，为—C(═O)—C1-C6-烷基，或—C(═O)-苯基，其中所述苯基未取代或可选地具有1至5个取代基，或者Ra和Rb一起是一个基团—(C═O)—或一个取代亚甲基基团—C(RdRe)—，Rc是基团RSi或苄基，其中所述苄基未取代或可选地具有1、2或3个取代基，RSi是具有式SiRfRgRh的基团，其中Rf、Rg和Rh相同或不同，为C1-C8-烷基，例如，R1是基团—C(═O)—R11或基团SiR12R13R14，R2相同或不同，为C1-C8-烷基，例如，R3相同或不同，例如为C1-C8-烷基，或两个基团R3一起形成未取代或具有1至6个甲基基团作为取代基的线性C1-C4-烯基。
• Kilogram scale chemical synthesis of 2′-fucosyllactose
  作者：Karoly Agoston、Markus Jondelius Hederos、Istvan Bajza、Gyula Dekany

  DOI：10.1016/j.carres.2019.03.006

  日期：2019.4

  A scalable synthetic procedure to high quality 2'-fucosyllactose, the most abundant oligosaccharide in human breast milk, has been designed and validated in kilogram scale. The synthetic route has been developed to suit industrial environment and contains only a single chromatographic purification step.