methyl 2,3,4-tri-O-acetyl-6-(tert-butyldimethylsiloxy)-β-D-galactopyranoside | 174618-10-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-acetyl-6-(tert-butyldimethylsiloxy)-β-D-galactopyranoside
• 英文别名: methyl 2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-β-D-galactopyranoside；TBDMS(-6)b-Gal1Me2Ac3Ac4Ac；[(2R,3S,4S,5R,6R)-4,5-diacetyloxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-methoxyoxan-3-yl] acetate
• CAS: 174618-10-1
• 化学式: C₁₉H₃₄O₉Si
• 分子量: 434.559
• InChiKey: DZCGETIINZOISC-DISONHOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-6-(tert-butyldimethylsiloxy)-β-D-galactopyranoside 在 溶剂黄146 作用下， 反应 2.0h， 以83%的产率得到methyl 2,3,4-tri-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and Biological Evaluation of N-Acetylneuraminic Acid-Based Rotavirus Inhibitors

  摘要：

  Rotavirus can cause several gastrointestinal disease, especially in infants and young children, and is particularly prevalent in Third-World countries. Therefore, the development of potential inhibitors of this virus is of great interest. The present study describes the synthesis and in vitro biological evaluation of a number of N-acethyneuraminic acid-based compounds as potential rotavirus inhibitors. Our data suggests that it is indeed possible to inhibit adhesion of the virus, and hence in vitro replication, with carbohydrate-based molecules, although this inhibition, dues appear to be strain dependent.

  DOI：

  10.1021/jm950611f
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 吡啶 作用下， 反应 24.0h， 生成 methyl 2,3,4-tri-O-acetyl-6-(tert-butyldimethylsiloxy)-β-D-galactopyranoside
  参考文献：
  名称：

  A Facile, One‐Step Conversion of 6‐O‐Trityl and 6‐O‐TBDMS Monosaccharides into the Corresponding Formate Esters

  摘要：

  A convenient method has been developed for a facile and high-yield conversion of 6-O-tertbutyldimethylsilyl and 6-O-trityl protected monosaccharides to their formate esters, which may serve as useful intermediates for the replacement of the primary hydroxyl group of sugars by other functional groups.

  DOI：

  10.1080/07328300600859668

文献信息

• DABCO: an efficient promoter for the acetylation of carbohydrates and other substances under solvent-free conditions
  作者：Ratnasekhar Ch、Mohit Tyagi、Premanand Ramrao Patil、K.P. Ravindranathan Kartha

  DOI：10.1016/j.tetlet.2011.08.141

  日期：2011.11

  A simple, mild and efficient solvent-free method for the acetylation of carbohydrates, and their partially protected derivatives, as well as non-carbohydrate substances in excellent yields in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) is described with the advantage of tolerance to various functional groups, short reaction time and ease of product isolation. (C) 2011 Elsevier Ltd. All rights reserved.
• Ravindranathan Kartha; Field, Synlett, 1999, # 3, p. 311 - 312
  作者：Ravindranathan Kartha、Field

  DOI：——

  日期：——