ethyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside | 201296-54-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside
• 英文别名: ethyl hepta-O-benzoyl-1-thio-β-lactoside；Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Gal(b1-4)[Bz(-2)][Bz(-3)][Bz(-6)]Glc(b)-SEt；[(2R,3S,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-2-(benzoyloxymethyl)-6-ethylsulfanyloxan-3-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 201296-54-0
• 化学式: C₆₃H₅₄O₁₇S
• 分子量: 1115.18
• InChiKey: VQGMFVKPDHWCNU-SOGVVDEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  81
• 可旋转键数：
  27
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  237
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  tetrakis-(hydroxymethyl)-tetrapropoxy-calix[4]arene 、 ethyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside 在 sodium methylate 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 生成
  参考文献：
  名称：

  Synthesis and Properties ofO-Glycosyl Calix[4]Arenes (Calixsugars)

  摘要：

  AbstractModelO‐glycosylation reactions at either rim of calix[4]arenes are described with the aim of providing access to a new family of carbohydrate‐containing calixarene derivatives named calixsugars. One or two sugar moieties (D‐mannofuranose and D‐glucopyranose) were introduced at the lower rim of the parent calix[4]arene by glycosylation of the phenolic hydroxyl groups by means of a Mitsunobu reaction. Tetrapropoxy calix[4]arenes bearing two or four hydroxymethyl groups at the upper rim were coupled with perbenzoylated thioethyl D‐galactoside and D‐lactoside in the presence of the thiophilic promoter copper(III) triflate. In this way β‐linked bis‐ and tetrakis‐O‐galactosyl calix[4]arenes were obtained in good yield, the latter showing some solubility in water. For theO‐lactosyl derivatives only the bis‐substituted compound could be obtained because of the competing formation of an intramolecular ether linkage between 1,3‐hydroxymethyl groups. Preliminary binding studies showed some affinity of the galactose‐containing calixsugars toward charged carbohydrates and dihydrogen phosphate anion.

  DOI：

  10.1002/chem.19970031108
• 作为产物：
  描述：

  苯甲酰氯 、 ethyl 4-O-β-galactopyranosyl-1-thio-β-D-glucopyranoside 在 吡啶 作用下， 反应 6.0h， 以75%的产率得到ethyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Properties ofO-Glycosyl Calix[4]Arenes (Calixsugars)

  摘要：

  AbstractModelO‐glycosylation reactions at either rim of calix[4]arenes are described with the aim of providing access to a new family of carbohydrate‐containing calixarene derivatives named calixsugars. One or two sugar moieties (D‐mannofuranose and D‐glucopyranose) were introduced at the lower rim of the parent calix[4]arene by glycosylation of the phenolic hydroxyl groups by means of a Mitsunobu reaction. Tetrapropoxy calix[4]arenes bearing two or four hydroxymethyl groups at the upper rim were coupled with perbenzoylated thioethyl D‐galactoside and D‐lactoside in the presence of the thiophilic promoter copper(III) triflate. In this way β‐linked bis‐ and tetrakis‐O‐galactosyl calix[4]arenes were obtained in good yield, the latter showing some solubility in water. For theO‐lactosyl derivatives only the bis‐substituted compound could be obtained because of the competing formation of an intramolecular ether linkage between 1,3‐hydroxymethyl groups. Preliminary binding studies showed some affinity of the galactose‐containing calixsugars toward charged carbohydrates and dihydrogen phosphate anion.

  DOI：

  10.1002/chem.19970031108

文献信息

• Benzoylated ethyl 1-thioglycosides: direct preparation from per-O-benzoylated sugars
  作者：Deepak Sail、Pavol Kováč

  DOI：10.1016/j.carres.2012.05.012

  日期：2012.8

  the beta-benzoate predominated. Treatment of the foregoing compounds with EtSH at slightly elevated temperature (50-60 degrees C) in the presence of BF(3).Et(2)O as a promoter gave the corresponding ethyl 1-thio glycosides in high yields. The alpha-products predominated in all cases in the anomeric mixtures formed. Individual products of all reactions were isolated by chromatography, they were obtained

  D-葡萄糖、乳糖、麦芽糖和蜜二糖用 Bz(2)O-Et(3)N 试剂苯甲酰化，得到完全苯甲酰化的 β 产品。在相同条件下，D-甘露糖产生了以 β-苯甲酸酯为主的混合物。在BF(3).Et(2)O作为促进剂存在下，在稍微升高的温度(50-60℃)下用EtSH处理上述化合物，以高产率得到相应的乙基1-硫代糖苷。在所有情况下，在所形成的异头混合物中，α-产物占主导地位。所有反应的各个产物均通过色谱法分离，获得分析纯状态的产物，并通过 (1)H 和 (13)C NMR 数据和物理常数进行充分表征。