6-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-2,3;4,6-di-O-isopropylidene-D-glucose dimethyl acetal | 77667-93-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-2,3;4,6-di-O-isopropylidene-D-glucose dimethyl acetal
• 英文别名: 4-O-(6-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal；6'-O-benzoyl-2,3:5,6:3',4'-tri-O-isopropylidenelactose dimethylacetal；6'-O-benzoyl-2,3:5,6:3',4'-tri-O-isopropylidenelactose；[(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]-7-hydroxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl benzoate
• CAS: 77667-93-7
• 化学式: C₃₀H₄₄O₁₃
• 分子量: 612.672
• InChiKey: ZHUKMZJNRAWGMI-DTQUUOPZSA-N

物化性质

• 沸点：
  695.6±55.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  6-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-2,3;4,6-di-O-isopropylidene-D-glucose dimethyl acetal 在 lithium aluminium tetrahydride 、 叠氮化四丁基铵 、 sodium hydride 作用下， 反应 6.67h， 生成 2,3-5,6-bis-O-isopropylidene-aldehydo-D-glucose dimethylacetal
  参考文献：
  名称：

  C-2 D'α-d-甘露聚糖和吡喃半乳糖苷中N-咪唑基磺酸盐的活化

  摘要：

  摘要乳糖衍生物3-甲基-O-苄基-4,6-O-亚苄基-α-d-甘露吡喃糖苷的N-咪唑基磺酰基衍生物，甲基3,4,6-三-O-苄基-α-d-甘露糖吡喃糖苷的乳糖衍生物除OH-2'，苄基6-O-烯丙基-3,4-O-异亚丙基-α-d-吡喃半乳糖苷和甲基3,4,6-三-O-甲基-β-d-吡喃半乳糖苷外，其他地方均受10个保护准备好了。甘露糖衍生物与叠氮化物在甲苯溶液中的反应产生适量的葡糖叠氮化物3和6，这可能是由于反式消除的普遍性所致。用一种半乳糖衍生物，即苄基2-乙酰氨基的前体，苄基6-O-烯丙基-2-叠氮基-2-脱氧-3，4-O-异亚丙基-α-d-塔洛吡喃糖苷获得了正常的取代产物。 -2-脱氧-α-d-塔洛吡喃糖苷。但是，主要反应始终是C-1取代的环收缩，导致差向异构体对12、13；14、15; 26，27; 和32，33。

  DOI：

  10.1016/s0008-6215(00)90130-7
• 作为产物：
  描述：

  Lactose 在 对甲苯磺酸 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 6-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-2,3;4,6-di-O-isopropylidene-D-glucose dimethyl acetal
  参考文献：
  名称：

  PROCESS FOR THE SYNTHESIS OF L-FUCOSYL DI- OR OLIGO-SACCHARIDES AND NOVEL 2,3,4 TRIBENZYL-FUCOSYL DERIVATIVES INTERMEDIATES THEREOF

  摘要：

  本发明涉及一种合成L-岩藻糖二糖或寡糖的过程，以及易于结晶的新型2,3,4-三-O-苄基-岩藻糖合成中间体衍生物。特别是，本发明涉及一种适用于工业规模的合成2'O-岩藻糖乳糖的过程。

  公开号：

  US20110245488A1

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。
• NOVEL METHOD FOR THE SYNTHESIS OF A TRISACCHARIDE
  申请人：Dékany Gyula

  公开号：US20120116065A1

  公开（公告）日：2012-05-10

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

  本发明涉及一种改进的三糖的合成方法，以及在合成过程中使用的新型中间体和中间体的制备。
• Synthesis of O-α-l-fucopyranosyl-(1→2)-O-β-d-galactopyranosyl-(1→4)-d-glucopyranose (2′-O-α-l-fucopyranosyl-lactose)
  作者：Saeed A. Abbas、Joseph J. Barlow、Khushi L. Matta

  DOI：10.1016/s0008-6215(00)84600-5

  日期：1981.1

  Abstract Selective benzoylation of 2,3:5,6:3′,4′-tri- O -isopropylidenelactose dimethyl acetal ( 1 ) with benzoyl chloride in dichloromethane afforded the 6′- O -benzoyl derivative ( 2 ). The constitution of 2 was inferred from its n.m.r. spectrum, and confirmed by methylation and subsequent hydrolysis to 2- O -methyl- d -galactose and d -glucose. Glycosidation of 2 (catalyzed by bromide ion) with

  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。
• SYNTHESIS AND APPLICATION OF SPACER-MODIFIED L-FUCOSE ANALOGUES1
  作者：Andrej-Jakob Ott、Meinolf Brackhagen、Anahit Davtyan、Birte Nolting、Hanna Boye、Astrid Schoknecht、Christian Vogel

  DOI：10.1081/car-100108277

  日期：——

  Starting from 6-O-tert-butyldimethylsilyl-2,3;4,5-di-O-isopropylidenealdehydo-D-galactose (1), the carbon backbone elongated GDP-L-fucose analogue 15 bearing a chromophore tag at the end of a spacer was synthesized. Additionally, the analogues of 3-L-fucosyllactose (29) and 2'-L-fucosyllactose (36), where the fucosyl moiety is marked by a five atom alkyl chain at C-5, were prepared as labeled oligosaccharides of human milk.
• [EN] PROCESS FOR THE SYNTHESIS OF L-FUCOSYL DI- OR OLIGOSACCHARIDES AND NOVEL 2,3,4 TRIBENZYL-FUCOSYL DERIVATIVES INTERMEDIATES THEREOF<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE DISACCHARIDES OU D'OLIGOSACCHARIDES DE L-FUCOSYLE ET DE NOUVEAUX INTERMÉDIAIRES DE CEUX-CI DU TYPE 2,3,4-TRIBENZYLFUCOSYLE
  申请人：INALCO SPA

  公开号：WO2010070616A8

  公开（公告）日：2011-07-28