2,3,4,2',3',4',6'-hepta-O-acetyl-6-O-trityl-α,α-trehalose | 113842-78-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2,3,4,2',3',4',6'-hepta-O-acetyl-6-O-trityl-α,α-trehalose
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(trityloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 113842-78-7
• 化学式: C₄₅H₅₀O₁₈
• 分子量: 878.881
• InChiKey: QNOICKKDMYXYFG-KIVRNGJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  63
• 可旋转键数：
  23
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  221
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  2,3,4,2',3',4',6'-hepta-O-acetyl-6-O-trityl-α,α-trehalose 在 二氯乙酸 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 17.5h， 生成 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-((methacryloyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  [EN] STABILIZATION OF BIOMOLECULES USING SUGAR POLYMERS
  [FR] STABILISATION DE BIOMOLÉCULES AU MOYEN DE POLYMÈRES DE GLUCIDES

  摘要：

  揭示了用于稳定生物分子的组合物和方法。具体来说，这些组合物包括含有与生物分子共轭的海藻糖侧链的新型同聚物或共聚物。当这种同聚物或共聚物与生物分子（如蛋白质）放置在紧密接触时，同聚物或共聚物可以保护和/或稳定生物分子。这些组合物和方法可能适用于各种行业，如医疗保健（制药）、分子生物学、生物燃料、纸张、个人护理、洗涤剂、摄影、橡胶、酿造、乳制品和食品加工行业。

  公开号：

  WO2013112897A1
• 作为产物：
  描述：

  海藻糖 在 吡啶 作用下， 反应 45.0h， 生成 2,3,4,2',3',4',6'-hepta-O-acetyl-6-O-trityl-α,α-trehalose
  参考文献：
  名称：

  [EN] STABILIZATION OF BIOMOLECULES USING SUGAR POLYMERS
  [FR] STABILISATION DE BIOMOLÉCULES AU MOYEN DE POLYMÈRES DE GLUCIDES

  摘要：

  揭示了用于稳定生物分子的组合物和方法。具体来说，这些组合物包括含有与生物分子共轭的海藻糖侧链的新型同聚物或共聚物。当这种同聚物或共聚物与生物分子（如蛋白质）放置在紧密接触时，同聚物或共聚物可以保护和/或稳定生物分子。这些组合物和方法可能适用于各种行业，如医疗保健（制药）、分子生物学、生物燃料、纸张、个人护理、洗涤剂、摄影、橡胶、酿造、乳制品和食品加工行业。

  公开号：

  WO2013112897A1

文献信息

• [EN] BIODEGRADABLE TREHALOSE GLYCOPOLYMERS<br/>[FR] GLYCOPOLYMÈRES BIODÉGRADABLES DE TRÉHALOSE
  申请人：UNIV CALIFORNIA

  公开号：WO2016025668A1

  公开（公告）日：2016-02-18

  Structures and methods of making biodegradable trehalose co-polymers are disclosed. Specifically, biodegradable trehalose co-polymers consist of the general structure R5-[R1R2C - CR3R4]n-[DG]m-R6, wherein R1-R4 are independently selected from hydrogen or a side chain comprising at least one carbon atom, and wherein at least one of R1-R4 is a side chain comprising -L-trehalose, wherein L is a linker molecule that links trehalose to the monomer through at least one of the trehalose hydroxyl groups (-OH), wherein DG is a biodegradable group, and wherein R5 and R6 are end groups.

  生物可降解海藻糖共聚物的结构和制备方法被披露。具体来说，生物可降解海藻糖共聚物由一般结构R5-[R1R2C - CR3R4]n-[DG]m-R6组成，其中R1-R4独立地选自氢或包含至少一个碳原子的侧链，且R1-R4中至少有一个是包含-L-海藻糖的侧链，其中L是将海藻糖通过至少一个海藻糖羟基（-OH）连接到单体的连接分子，DG是一个生物可降解基团，R5和R6是末端基团。
• Inhibition of <i>S. aureus</i> Infection of Human Umbilical Vein Endothelial Cells (HUVECs) by Trehalose‐ and Glucose‐Functionalized Gold Nanoparticles
  作者：Yimeng Li、Nicholas Ariotti、Behnaz Aghaei、Elvis Pandzic、Sylvia Ganda、Mark Willcox、Manuel Sanchez‐Felix、Martina Stenzel

  DOI：10.1002/anie.202106544

  日期：2021.10.11

  ability to prevent binding to endothelial cells. Acting as anti-adhesive agents, trehalose-functionalized NPs decreased the binding of S. aureus to HUVECs, while outperforming the control NPs. Microscopy revealed that trehalose-coated NPs bound strongly to S. aureus compared to the controls. In conclusion, nanoparticles based on trehalose could be a non-toxic alternative to inhibit S. aureus infection

  微生物对宿主细胞的粘附是感染过程的第一步。已经探索了几种抑制微生物粘附的方法，包括使用基于甘露糖、半乳糖、唾液酸和葡萄糖的糖聚合物。然而，这些糖受体在体内大量存在，并非细菌所独有。相比之下，海藻糖是一种独特的二糖，被微生物广泛表达。这种碳水化合物还没有被用作抗粘剂。在此，制备了涂有海藻糖基聚合物的金纳米粒子 (AuNPs)，并与葡萄糖功能化的 AuNPs 进行了比较，并检查了它们防止与内皮细胞结合的能力。作为抗粘剂，海藻糖功能化的 NPs 降低了金黄色葡萄球菌的结合到 HUVEC，同时优于对照 NP。显微镜显示，与对照相比，海藻糖包被的 NPs 与金黄色葡萄球菌结合牢固。总之，基于海藻糖的纳米颗粒可能是抑制金黄色葡萄球菌感染的无毒替代品。
• Glycosylated trehalose. Synthesis of the oligosaccharides of the glycolipid-type antigens from Mycobacterium smegmatis
  作者：Zoltán Szurmai、János Kerékgyártó、János Harangi、András Lipták

  DOI：10.1016/0008-6215(87)80138-6

  日期：1987.7

  The oligosaccharide components, 3-O-Me-beta-D-Glcp-(1----3)-beta-D-Glcp-(1----4)-beta-D-Glcp-(1----6)- alpha-D-Glcp-(1----1)-alpha-D-Glcp (1) and beta-D-Glcp-(1----4)-beta-D-Glcp-(1----6)-alpha-D-Glcp-(1----1)-alpha-D- Glcp, of the glycolipid-type antigens isolated from M. smegmatis have been synthesised from 2,3,4,2',3',4',6'-hepta-O-acetyl-alpha,alpha-trehalose and the appropriate glycosyl bromides

  寡糖成分3-O-Me-beta-D-Glcp-（1 ---- 3）-beta-D-Glcp-（1 ---- 4）-beta-D-Glcp-（1- --6）-alpha-D-Glcp-（1 ---- 1）-alpha-D-Glcp（1）和beta-D-Glcp-（1 ---- 4）-beta-D-Glcp-从耻垢分枝杆菌分离的糖脂型抗原中的（1 ---- 6）-α-D-Glcp-（1 ---- 1）-α-D-Glcp已从2,3,4合成，2'，3'，4'，6'-庚-O-乙酰基-α，α-海藻糖和适当的糖基溴化物在Helferich条件下以Hg（CN）2为促进剂。三糖糖基溴化物27的缩合得到原酸酯衍生物（28），可以使用HgBr2或三氟化硼醚化物将其重新排列成1的乙酰化衍生物（29）。模型化合物β-D-Glcp-（1 --- -6）-α-D-Glcp-（1 ---- 1）-α-D-Glcp也已经合成。
• Substituted polyesters by thiol-ene modification: rapid diversification for therapeutic protein stabilization
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US10273333B2

  公开（公告）日：2019-04-30

  Structures and methods of making biodegradable trehalose co-polymers are disclosed. Specifically, biodegradable trehalose co-polymers consist of the general structure R5—[R1R2C—CR3R4]n-[DG]m—R6, wherein R1-R4 are independently selected from hydrogen or a side chain comprising at least one carbon atom, and wherein at least one of R1-R4 is a side chain comprising -L-trehalose, wherein L is a linker molecule that links trehalose to the monomer through at least one of the trehalose hydroxyl groups (—OH), wherein DG is a biodegradable group, and wherein R5 and R6 are end groups.

  本发明公开了可生物降解的三卤糖共聚物的结构和制造方法。具体来说，可生物降解的三卤糖共聚物由一般结构 R5-[R1R2C-CR3R4]n-[DG]m-R6组成，其中 R1-R4 独立地选自氢或包含至少一个碳原子的侧链、其中 R1-R4 中至少有一个是由-L-曲哈糖组成的侧链，其中 L 是连接分子，通过至少一个曲哈糖羟基（-OH）将曲哈糖与单体连接，其中 DG 是可生物降解基团，其中 R5 和 R6 是端基。
• Synthetic studies toward pyruvate acetal containing saccharides. Synthesis of the carbohydrate part of the Mycobacterium smegmatis pentasaccharide glycolipid and fragments thereof for the preparation of neoantigens
  作者：Thomas Ziegler、Elisabeth Eckhardt、Veronique Birault

  DOI：10.1021/jo00057a021

  日期：1993.2

  A series of 2,3-di-O-benzoyl-4,6-O-[(S)-1-(methoxycarbonyl)ethylidene]-D-glucopyranosyl donors (beta-phenylthio 3, bromide 4, alpha-chloride 5, beta-fluoride 6, and trichloroacetimidate 7) were prepared from the corresponding alpha-allyl glucoside 1 via the deallylated glucose 2 and were tested in glycosylation reactions with methanol to give the pyruvylated methyl glucosides 8 and 9 and with methyl 2,4,6-tri-O-benzoyl-beta-D-glucopyranoside 10 to give the disaccharide 11. Best results with respect to yield and beta-selectivity of the coupling were achieved with imidate 7. Thus, the 2-O-benzoyl-4,6-O-[(S)-1-(methoxycarbonyl)ethylidene]-3-O-methyl-D-glucopyranosyl trichloroacetimidate 14 was prepared from its benzyl glucoside 12 and used for the synthesis of fragments related to the Mycobacterium smegmatis lipopentasaccharide. Trimethylsilyl trifluoromethanesulfonate-mediated condensation of 14, 5-[(benzyloxycarbonyl)amino]pentanol, and 10, respectively, followed by deblocking of the products 15 and 17 gave the pyruvylated aminopentyl glucoside 16 and methyl laminaribioside 18. Treatment of 17 with dichloromethyl methyl ether gave the laminaribiosyl chloride 19, coupling of which with protected 5-aminopentanol gave 20 also obtained from 14 and the monosaccharide nucleophile 26. The trisaccharide 5-aminopentyl glycoside fragment 42 was prepared by first coupling of 14 and benzyl 2-O-benzoyl-4,6-O-[(S)-1-(methoxycarbonyl)ethylidene]-alpha-D-glucopyranoside 30 that was converted to the bispyruvylated laminaribiose imidate 33, followed by condensation with thioglycoside 38 obtainable in four steps from 1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose to give the trisaccharide ethyl thioglycoside 40. Next, NIS-mediated condensation of 40 and 5-[(benzyloxycarbonyl)amino]pentanol followed by deblocking gave 42. Pentasaccharide 45 was similarly prepared from 40 and hepta-O-benzoyltrehalose 43 to give first the blocked saccharide 44, deblocking of which afforded the target pentasaccharide.