2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside | 148852-74-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside
• CAS: 148852-74-8
• 化学式: C₂₈H₄₀O₆Si
• 分子量: 500.707
• InChiKey: RBWHFLHHUBHWCW-LXSUACKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  35.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside 在 palladium on activated charcoal 、 palladium hydroxide - carbon 4 A molecular sieve 、 Ag-silicate on alumina 、 氢气 、 溶剂黄146 作用下， 以 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， -15.0~60.0 ℃ 、17.2 MPa 条件下， 反应 76.0h， 生成
  参考文献：
  名称：

  The synthesis of 16-mercaptohexadecanyl glycosides for biosensor applications

  摘要：

  The P-k trisaccharide and the central disaccharide element of asialo GM(1) activated as their trichloroacetimidates were each used to glycosylate 16-(p-toluensulfonyloxy)hexadecanol 1. Displacement of the tosyl group by thiocyanate followed by sodium borohydride reduction and saponification afforded oligosaccharide 16-mercaptohexadecanyl glycosides that were isolated as the corresponding disulfides 6 and 17 unless oxygen was rigorously excluded from the solvents used for work-up. Dithiothreitol reduction of disulfides and subsequent isolation under an inert atmosphere with degassed solvents gave the thiols 7 and 18. Chemisorption of omega-glycosyl alkanethiols and alkanethiols onto gold electrodes produces self-assembled monolayers that can act as amperometric biosensors for the detection of proteins that bind to the immobilized oligosaccharide epitope. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00053-6
• 作为产物：
  描述：

  2-(三甲基硅烷基)乙基beta-吡喃半乳糖苷 在 硫酸 、 sodium hydride 、 N,N-二甲基甲酰胺 作用下， 以 丙酮 为溶剂， 反应 26.25h， 生成 2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside
  参考文献：
  名称：

  磷酸化半乳糖衍生物的合成及类胰岛素活性

  摘要：

  已进行了分离为钠盐的多磷酸化半乳糖苷6、8、10、13、16和20的合成。分别通过2-（三甲基甲硅烷基）乙基半乳糖苷3和2的糖基化以及随后的完全脱保护来制备非磷酸化的二糖17和三糖21。磷酸化衍生物的初步胰岛素样活性已有报道。

  DOI：

  10.1016/0008-6215(93)84177-8

文献信息

• Synthesis of a Blocked Tetrasaccharide Related to the Repeating Unit of the Antigen from <i>Shigella dysenteriae</i> Type 9 in the Form of Its Methyl (<i>R</i>)‐Pyruvate Ester and 2‐(Trimethylsilyl)Ethyl Glycoside
  作者：Samarpita Roy、Nirmolendu Roy

  DOI：10.1081/car-120026456

  日期：2003.12.31

  Starting from D-mannose, D-galactose and D-glucosamine hydrochloride, two disaccharide blocks were synthesized. Schmidt's inverse addition technique of trichloroacetimidate was utilized for the construction of a disaccharide with a beta-mannosidic linkage in good yield. The other disaccharide had a methyl 4,6-(R)pyruvate ester. The two disaccharides in the appropriate form were then allowed to react in the presence of N-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH) to give the desired tetrasaccharide derivative, 2-(trimethylsilyl)ethyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-beta-D-glucopyranosyl-(l --> 3)-2-O-benzoyl-4,6-O-[(R)-1-methoxycarbonylethylidene]-beta-D-galactopyranosyl-(I --> 4)-2,3,6-tri-O-benzyl-beta-D-mannopyranosyl-(1 --> 4)-2,6-di-O-benzyl-3-O-(4-methoxybenzyl)-beta-D-galactopyranoside.