2,3,6-tri-O-benzyl-α-D-glucopyranosyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside | 136090-72-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,6-tri-O-benzyl-α-D-glucopyranosyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-5-hydroxy-3,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-ol
• CAS: 136090-72-7
• 化学式: C₅₄H₅₈O₁₁
• 分子量: 883.048
• InChiKey: DDJAZHRJJSZXAL-IPCGEZBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  65
• 可旋转键数：
  22
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,6-tri-O-benzyl-α-D-glucopyranosyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Convenient Divergent Synthesis of a Library of Trehalosamine Analogues

  摘要：

  A library of seven trehalosamine analogues with various natural and non-natural binding motifs was synthesized through an expedient divergent synthetic approach, The final products were prepared in sufficient quantities and purities for different types of assay against various pathogens. Several stereo- and regioselective reactions on the trehalose scaffold were developed for rapid synthesis of all of the designed compounds.

  DOI：

  10.1021/ol026095m
• 作为产物：
  描述：

  海藻糖 在 盐酸 、 氢气 、 potassium hydride 、 sodium cyanoborohydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2,3,6-tri-O-benzyl-α-D-glucopyranosyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Water-Soluble Organometallic Catalysts from Carbohydrates. 1. Diphosphinite−Rh Complexes

  摘要：

  [GRAPHICS]Cyclohexylidene-protected diphosphinite-Rh complex A derived from alpha,alpha'-trehalose was treated with acidic resin in methanol to get the unprotected complex B, which is water soluble. Preparation of complexes A-C and their applications for hydrogenations show the problems and prospects of using water as a solvent for these reactions.

  DOI：

  10.1021/ol9908979

文献信息

• Synthesis, trehalase hydrolytic resistance and inhibition properties of 4- and 6-substituted trehalose derivatives
  作者：Shari Dhaene、Johan Van der Eycken、Koen Beerens、Jorick Franceus、Tom Desmet、Jurgen Caroen

  DOI：10.1080/14756366.2020.1837125

  日期：2020.1.1

  activity could be of interest. In this study, 34 4- and 6-O-substituted trehalose derivatives were synthesised using an ether- or carbamate-type linkage. Their hydrolysis susceptibility and inhibitory properties were determined against two trehalases, i.e. porcine kidney and Mycobacterium smegmatis. With the exception of three weakly hydrolysable 6-O-alkyl derivatives, the compounds generally showed to be

  摘要 尽管海藻糖由于其药物潜力最近已引起人们的兴趣，但由于其生物利用度低而阻碍了其临床应用。因此，保持生物活性的耐水解的海藻糖类似物可能是令人感兴趣的。在这项研究中，使用醚或氨基甲酸酯型键合成了34种4-和6- O取代的海藻糖衍生物。测定了它们对两种海藻糖酶的水解敏感性和抑制特性，即猪肾和耻垢分枝杆菌。除了三个弱水解的6- O-烷基衍生物，该化合物通常显示出完全抗性。此外，许多衍生物被证明是这些海藻糖酶之一或两者的抑制剂。对于猪肾海藻糖酶的最强抑制剂，可以测定约50 mM的IC 50值，而几种化合物显示出针对耻垢分枝杆菌海藻糖酶的亚mM IC 50值。进行了对接研究以解释观察到的取代模式对猪肾海藻糖酶抑制活性的影响。
• ?-D-Glycosyl-Substituted ?,?-D-Trehaloses with (1 ? 4)-Linkage: Syntheses and NMR Investigations
  作者：Hans Peter Wessel、Gerhard Englert、Peter Stangier

  DOI：10.1002/hlca.19910740403

  日期：1991.6.19

  Two symmetrical trehalose glycosyl ‘acceptors’ 4 and 6 were prepared and three of the unsymmetrical type, 8, 10, and 11. Glucosylation of symmetrical ‘acceptor’ 4 gave a higher yield of trisaccharide (44%) than protect ve-group manipulation, namely via selective debenzylidenation 2 9 or monoacetylation 2 5 which proceeded in moderate yields (33–34%). A comparison of catalysts in the cis-glucosylation

  两个对称的海藻糖的糖基“受体” 4和6中制备和三个非对称型的，8，10，和11。对称的“受体” 4的糖基化比保护ve-基团操纵（即通过选择性脱苄基2 9或单乙酰化2 5）获得的三糖收率更高（44％），中等收率（33-34％）。海藻糖“受体” 10与四-O-苄基-β-D-吡喃葡萄糖基氟13的顺式-葡萄糖基化反应中催化剂的比较异三氟甲磺酸酐（（Tf）2 O）作为新的反应性启动子，产生92％的三糖14，解封得到目标糖α-D-吡喃葡萄糖基-（1 4）-α，α-D-海藻糖。对大多数化合物的1 H-NMR光谱进行了广泛的分析。提倡使用ID TOCSY技术的时间效率，如果需要的话还可以通过ROESY实验进行补充。
• Synthesis of mono- and dideoxygenated α,α-trehalose analogs
  作者：Fiona L. Lin、Herman van Halbeek、Carolyn R. Bertozzi

  DOI：10.1016/j.carres.2007.05.009

  日期：2007.10

  the synthesis and NMR characterization of four mono- and four dideoxygenated analogs of α,α- d -trehalose. The symmetrical (2,2′-, 3,3′-, 4,4′- and 6,6′-) dideoxy analogs were obtained via selective protection and subsequent radical deoxygenation of the desired hydroxyl group set. The unsymmetrical (2′-, 3′-, 4′- and 6′-) monodeoxy analogs were synthesized by desymmetrization of α,α-trehalose and subsequent

  摘要在本文中，我们描述了α，α-d-海藻糖的四个单脱氧和四个双脱氧类似物的合成和NMR表征。对称的（2,2'-，3,3'-，4,4'-和6,6'-）双脱氧类似物是通过选择性保护和随后的所需羟基组的自由基脱氧而获得的。通过α，α-海藻糖的脱对称和随后在自由基条件下的脱氧合成不对称的（2'-，3'-，4'-和6'-）单脱氧类似物。通过广泛使用2D 1 H，1 H}和1 H，13 C}相关NMR实验，可以实现这些脱氧海藻糖光谱中所有1 H和13 C共振的完全分配。
• Method for Producing Lentztrehalose A, Compound Useful for the Method, and Method for Producing the Compound
  申请人：Microbial Chemistry Research Foundation

  公开号：US20160362437A1

  公开（公告）日：2016-12-15

  A method for producing a compound represented by Structural Formula (1), including: introducing benzyl group into trehalose to produce at least one of compound represented by Structural Formula 4a and compound represented by Structural Formula 4a′; subjecting at least one of the Structural Formula 4a compound and the Structural Formula 4a′ compound to prenylation to produce at least one of compound represented by Structural Formula 3a and compound represented by Structural Formula 3a′; subjecting at least one of the Structural Formula 3a compound and the Structural Formula 3a′ compound to sharpless asymmetric dihydroxylation to produce at least one of compound represented by Structural Formula 2a and compound represented by Structural Formula 2a′; and allowing at least one of the Structural Formula 2a compound and the Structural Formula 2a′ compound to react with hydrogen in the presence of palladium catalyst to produce the compound represented by Structural Formula (1).

  一种制备结构式（1）所代表化合物的方法，包括以下步骤：将苯甲基引入海藻糖中，制备出结构式4a和结构式4a′所代表的化合物中的至少一种；将结构式4a化合物和结构式4a′化合物中的至少一种进行异戊烯化反应，制备出结构式3a和结构式3a′所代表的化合物中的至少一种；将结构式3a化合物和结构式3a′化合物中的至少一种进行Sharpless不对称二羟基化反应，制备出结构式2a和结构式2a′所代表的化合物中的至少一种；在钯催化剂的存在下，将结构式2a化合物和结构式2a′化合物中的至少一种与氢反应，制备出结构式（1）所代表的化合物。
• Synthesis of trehalose-based compounds and their inhibitory activities against Mycobacterium smegmatis
  作者：Jinhua Wang、Bryan Elchert、Yu Hui、Jon Y. Takemoto、Mekki Bensaci、John Wennergren、Huiwen Chang、Ravi Rai、Cheng-Wei Tom Chang

  DOI：10.1016/j.bmc.2004.09.033

  日期：2004.12

  The synthesis of a library of trehalose-based compounds has been accomplished, and their activities against mycobacterium smegmatis have been determined. A preliminary structure-activity relationship (SAR) is reported. Despite not having a potent lead, one of the trehalose derivatives displays strong activity when applied with isoniazid (INH), which is known to have low sterilizing activity. The bacteriocidal nature of our compounds against Mycobacterium may be significant for the development of new therapies against tuberculosis. (C) 2004 Elsevier Ltd. All rights reserved.