benzyl O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 62867-79-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: benzyl O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside；benzyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside；Bn(-2)[Bn(-3)][Bn(-6)]Gal(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]Glc(b)-O-Bn；(2R,3S,4S,5R,6S)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-[(2R,3R,4S,5R,6R)-4,5,6-tris(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxyoxan-3-ol
• CAS: 62867-79-2
• 化学式: C₆₁H₆₄O₁₁
• 分子量: 973.173
• InChiKey: PSCOLXWCXLWMLX-IMBADGMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  72
• 可旋转键数：
  25
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  benzyl O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 硫代乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 49.5h， 生成 benzyl (2-N-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic Ligands For The Differentiation Of Closely Related Toxins And Pathogens

  摘要：

  本文揭示了合成配体化合物和区分志贺毒素1和志贺毒素2的方法。另一实施例包括用于区分志贺毒素1和志贺毒素2的试剂盒。还提供了用于提供测定的测定系统和方法。

  公开号：

  US20090042816A1
• 作为产物：
  描述：

  Benzyl 4,6-O-benzyliden β-lactosid 在 氢氧化钾 作用下， 反应 3.0h， 生成 benzyl O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Paulsen, Hans; Buensch, Almuth, Liebigs Annalen der Chemie, 1981, # 12, p. 2204 - 2215

  摘要：

  DOI：

文献信息

• Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners
  作者：Mohamed Ramadan El Sayed Aly、Hosam Ali Saad、Shams Hashim Abdel-Hafez

  DOI：10.3762/bjoc.11.208

  日期：——

  3β-Azidocholest-5-ene (3) and (3β)-3-(prop-2-yn-1-yloxy)cholest-5-ene (10) were prepared as substrates to synthesize a variety of three-motif pharmacophoric conjugates through CuAAC. Basically, these conjugates included cholesterol and 1,2,3-triazole moieties, while the third, the pharmacophore, was either a chalcone, a lipophilic residue or a carbohydrate tag. These compounds were successfully prepared in good yields and characterized by NMR, MS and IR spectroscopic techniques. Chalcone conjugate 6c showed the best antimicrobial activity, while the lactoside conjugate 27 showed the best cytotoxic effect in vitro.

  3β-氮杂胆甾-5-烯（3）和（3β）-3-(丙-2-炔-1-氧基)胆甾-5-烯（10）被制备为底物，以合成各种三基团药效团结合物通过CuAAC。基本上，这些结合物包括胆固醇和1,2,3-三唑基团，而第三个药效团则是香豆素、疏水残基或碳水化合物标记中的一个。这些化合物以良好的产率成功制备，并通过NMR、MS和IR光谱技术进行表征。香豆素结合物6c显示出最佳的抗微生物活性，而乳糖苷结合物27在体外显示出最佳的细胞毒作用。
• Total synthesis of globotriaosyl-E and Z-ceramides and isoglobotriaosyl-E-ceramide
  作者：Katsuya Koike、Mamoru Sugimoto、Susumu Sato、Yukishige Ito、Yoshiaki Nakahara、Tomoya Ogawa

  DOI：10.1016/0008-6215(87)80181-7

  日期：1987.6

  Stereoselective, total synthesis of O-alpha-D-galactopyranosyl-(1----4) -O-beta-D-galactopyranosyl-(1----4)-O-beta-D-glucopyranosyl-(1----1)-N -tetracosanoyl-[2S,3R,4E (and 4Z)]-sphingenine and O-alpha-D -galactopyranosyl-(1----3)-O-beta-D-galactopyranosyl-(1----4)-O-beta-D -glucopyranosyl-(1----1)-N-tetracosanoyl-(2S,3R,4E)-sphin gen ine was achieved by using O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)

  O-α-D-吡喃半乳糖基-（1 ---- 4）-O-β-D-吡喃半乳糖基-（1 ---- 4）-O-β-D-吡喃葡萄糖基-（1-的立体选择性全合成--- 1）-N-十四烷酰基-[2S，3R，4E（和4Z）]-鞘氨醇和O-α-D-吡喃半乳糖基-（1 ---- 3）-O-β-D-吡喃半乳糖基-（通过使用O-（2,3）可实现1 ---- 4）-O-β-D-吡喃葡萄糖基-（1 ---- 1）-N-十四烷酰基-（2S，3R，4E）-斯宾碱，4,6-四-O-乙酰基-α-D-吡喃半乳糖基）-（1 ---- 4）-O-（2,3,6-三-O-乙酰基-β-D-吡喃半乳糖基）-（ 1 ---- 4）-2,3,6-三-O-乙酰基-α-D-吡喃葡萄糖基三氯乙酰亚氨酸酯，O-（2,3,4,6-四-O-乙酰基-α-D-吡喃半乳糖基） -（1 ---- 4）-O-（2,3,6-三-O-乙酰基-β-D-吡喃半乳糖基）-（1
• A stereocontrolled total synthesis of a ganglio-ganglioside GM1b, IV3NeuAcαGgOse4Cer
  作者：Mamoru Sugimoto、Kazushige Fujikura、Shigeki Nunomura、Toshio Horisaki、Yukishige Ito、Tomoya Ogawa

  DOI：10.1016/s0040-4039(00)94561-1

  日期：1990.1

  A first total synthesis of ganglio ganglioside GM1b. α-D-NeupAc-(2→3)-β-D-Galp(1→3)-β-D-GalpNAc-(1→4)-β-D-Galp-(1→4)-β-D-Glcp-(1→1)-Cer, was achieved in a stereocontrolled manner.

  的第一全合成ganglio神经节苷脂GM1b。α-d-neu的p的Ac-（2→3）-β-d-Gal的p（1→3）-β-d-Gal的p NAc-（1→4）-β-d-Gal的p - （1→ 4）-β-d-GLC p - （1→1）-Cer，在一个立体控制的方式来实现。
• Bishydrazide Glycoconjugates for Lectin Recognition and Capture of Bacterial Pathogens
  作者：Avijit Kumar Adak、Alexei P. Leonov、Ning Ding、Jyothi Thundimadathil、Sumith Kularatne、Philip S. Low、Alexander Wei

  DOI：10.1021/bc100288c

  日期：2010.11.17

  Bishydrazides are versatile linkers for attaching glycans to substrates for lectin binding and pathogen detection schemes. The alpha,omega-bishydrazides of carboxymethylated hexa(ethylene glycol) (4) can be conjugated at one end to unprotected oligosaccharides, then attached onto carrier proteins, tethered onto activated carboxyl-terminated surfaces, or functionalized with a photoactive cross-linking agent for lithographic patterning. Glycoconjugates of bishydrazide 4 can also be converted into dithiocarbamates (DTCs) by treatment with CS2 under mild conditions, for attachment onto gold substrates. The immobilized glycans serve as recognition elements for cell-surface lectins and enable the detection and capture of bacterial pathogens such as Pseudomonas aeruginosa by their adsorption onto micropatterned substrates. A detection limit of 10(3) cfu/mL is demonstrated, using a recently introduced method based on optical pattern recognition.
• Qiu, Dongxu; Schmidt, Richard R., Liebigs Annalen der Chemie, 1992, # 3, p. 217 - 224
  作者：Qiu, Dongxu、Schmidt, Richard R.

  DOI：——

  日期：——