methyl 3-tert-butyldiphenylsilyl-(2R)-2-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)glycerate | 1096143-69-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-tert-butyldiphenylsilyl-(2R)-2-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)glycerate
• 英文别名: methyl 3-O-tert-butyldiphenylsilyl-(2R)-2-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-2,3-dihydroxypropanoate；methyl (2R)-3-[tert-butyl(diphenyl)silyl]oxy-2-[(2R,3R,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxypropanoate
• CAS: 1096143-69-9
• 化学式: C₄₇H₅₄O₉Si
• 分子量: 791.026
• InChiKey: KYNGSXWXEUKUAU-CQVCTRCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.59
• 重原子数：
  57
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 3-tert-butyldiphenylsilyl-(2R)-2-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)glycerate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以90%的产率得到methyl (2R)-2-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)glycerate
  参考文献：
  名称：

  （2R）-2-O-α-d-吡喃葡萄糖基-（1-> 6）-α-d-吡喃葡萄糖基-2,3-二羟基丙酸钾的合成是天然的溶质。

  摘要：

  作为异构体的混合物，将乙基6-O-乙酰基-2,3,4-三苄基-1-硫代-d-吡喃葡萄糖苷用于（2R）-2-O-α-钾盐的立体选择性合成d-吡喃葡萄糖基-（1-> 6）-α-d-吡喃葡萄糖基-2,3-二羟基丙酸（α-d-葡萄糖基-（1-> 6）-alpha-d-葡萄糖基-（1-- > 2）-d-甘油酸（GGG），最近分离出的相容溶质。到目前为止，使用NIS / TfOH作为活化剂，α-端基异构体是两个糖基化反应的主要产物。

  DOI：

  10.1016/j.carres.2009.06.037
• 作为产物：
  描述：

  methyl 3-tert-butyldiphenylsilyl-(2R)-2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)glycerate 在 甲醇 、 sodium 作用下， 反应 0.5h， 以94%的产率得到methyl 3-tert-butyldiphenylsilyl-(2R)-2-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)glycerate
  参考文献：
  名称：

  （2R）-2-O-α-d-吡喃葡萄糖基-（1-> 6）-α-d-吡喃葡萄糖基-2,3-二羟基丙酸钾的合成是天然的溶质。

  摘要：

  作为异构体的混合物，将乙基6-O-乙酰基-2,3,4-三苄基-1-硫代-d-吡喃葡萄糖苷用于（2R）-2-O-α-钾盐的立体选择性合成d-吡喃葡萄糖基-（1-> 6）-α-d-吡喃葡萄糖基-2,3-二羟基丙酸（α-d-葡萄糖基-（1-> 6）-alpha-d-葡萄糖基-（1-- > 2）-d-甘油酸（GGG），最近分离出的相容溶质。到目前为止，使用NIS / TfOH作为活化剂，α-端基异构体是两个糖基化反应的主要产物。

  DOI：

  10.1016/j.carres.2009.06.037

文献信息

• The effect of electron withdrawing protecting groups at positions 4 and 6 on 1,2-cis galactosylation
  作者：Eva C. Lourenço、M. Rita Ventura

  DOI：10.1016/j.tet.2013.06.038

  日期：2013.8

  Ethyl 2,3,4-O-tribenzyl-6-O-chloroacetyl-1-D-thiogalactoside, phenyl 4,6-O-diacetyl-2,3-dibenzyl-1-D-thiogalactoside and phenyl 2,3-O-dibenzyl-4,6-O-dichloroacetyl-1-D-thiogalactoside were employed in the study of the stereoselectivity of the glycosylation reaction with several acceptors, ranging from unhindered linear primary alcohols to other sugars, using NIS/TfOH as activator. Higher alpha-selectivities were obtained in the glycosylation reactions with phenyl 2,3-O-dibenzyl-4,6-O-dichloroacetyl-1-D-thiogalactoside as the donor, showing that a stronger electron withdrawing 4-O-ester group had an influence in the anomeric selectivity favouring the formation of 1,2-cis galactosides. (C) 2013 Elsevier Ltd. All rights reserved.
• Design of new enzyme stabilizers inspired by glycosides of hyperthermophilic microorganisms
  作者：Tiago Q. Faria、Ana Mingote、Filipa Siopa、Rita Ventura、Christopher Maycock、Helena Santos

  DOI：10.1016/j.carres.2008.08.030

  日期：2008.12

  In response to stressful conditions like supra-optimal salinity in the growth medium or temperature, many microorganisms accumulate low-molecular-mass organic compounds known as compatible solutes. In contrast with mesophiles that accumulate neutral or zwitterionic compounds, the solutes of hyperthermophiles are typically negatively charged. (2R)-2-(alpha-D-Mannopyranosyl)glycerate (herein abbreviated as mannosylglycerate) is one of the most widespread solutes among thermophilic and hyperthermophilic prokaryotes. In this work, several molecules chemically related to mannosylglycerate were namely (2S)-2-(1-O-alpha-D-mannopyranosyl)propionate, 2-(1-O-alpha-D-mannopyranosyl)acetate, synthesized, (2R)-2-(1-O-alpha-D-glucopyranosyl)glycerate and 1-O-(2-glyceryl)-alpha-D-mannopyraiioside. The effectiveness of the newly synthesized compounds for the protection of model enzymes against heat-induced denaturation, aggregation and inactivation was evaluated, using differential scanning calorimetry, light scattering and measurements of residual activity. For comparison, the protection induced by natural compatible solutes, either neutral (e.g., trehalose, glycerol, ectoine) or negatively charged (di-myo-inositol-1,3 '-phosphate and diglycerol phosphate), was assessed. Phosphate, sulfate, acetate and KCl were also included in the assays to rank the solutes and new compounds in the Hofmeister series. The data demonstrate the superiority of charged organic solutes as thermo-stabilizers of enzymes and strongly support the view that the extent of protein stabilization rendered by those solutes depends clearly on the specific solute/enzyme examined. The relevance of these findings to our knowledge on the mode of action of charged solutes is discussed. (C) 2008 Elsevier Ltd. All rights reserved.