对硝基苯基 6-O-三苯甲基-alpha-D-吡喃葡萄糖苷 | 655246-35-8

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: 对硝基苯基 6-O-三苯甲基-alpha-D-吡喃葡萄糖苷
• 中文别名: 4-硝基苯基6-O-三苯甲基-aD-吡喃葡萄糖苷；4-硝基苯基-6-O-三苯甲基-Α-D-吡喃葡萄糖苷
• 英文名称: p-nitrophenyl 6-O-trityl-α-D-glucopyranoside
• 英文别名: 4-Nitrophenyl 6-O-trityl-a-D-glucopyranoside；(2R,3R,4S,5S,6R)-2-(4-nitrophenoxy)-6-(trityloxymethyl)oxane-3,4,5-triol
• CAS: 655246-35-8
• 化学式: C₃₁H₂₉NO₈
• 分子量: 543.573
• InChiKey: HUYKQPASBOHHIN-RLXMVLCYSA-N

物化性质

• 熔点：
  65-67°C
• 沸点：
  727.8±60.0 °C(Predicted)
• 密度：
  1.353±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  对硝基苯基 6-O-三苯甲基-alpha-D-吡喃葡萄糖苷 在 吡啶 、 甲酸 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-nitrophenyl 2,3,4-tri-O-benzoyl-6-O-[2',3',4',6'-tetra-O-benzoyl-5'-deoxy-5'-thio-D-glucopyranosyl]-α-D-glucopyranoside
  参考文献：
  名称：

  Synthetic studies on oligosaccharides composed of 5-thioglucopyranose units

  摘要：

  Glycosylation reactions of 5-thioglucopyranosyl trichloroacetimidates bearing ethereal protective groups at the 2-O-position 14-15, and 37 proceed smoothly to give alpha-glycosides stereoselectively by using a catalytic amount of silyl triflate. This methodology allowed us to achieve syntheses of sulfur-substituted isomaltotetraoside 2 and maltotetraoside 3. These studies also revealed that benzoyl-protected 5-thioglucopyranosyl trichloroacetimidate 12 underwent P-selective glycosylation with C6-OH glucopyranosyl acceptors upon activation by BF3OEt2. This was applied for preparation of sulfur-substituted gentiobiosides 1 and 46. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.028
• 作为产物：
  描述：

  三苯基氯甲烷 、 对硝基苯-α-D-葡萄糖吡喃苷 在 吡啶 作用下， 生成 对硝基苯基 6-O-三苯甲基-alpha-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Synthetic studies on oligosaccharides composed of 5-thioglucopyranose units

  摘要：

  Glycosylation reactions of 5-thioglucopyranosyl trichloroacetimidates bearing ethereal protective groups at the 2-O-position 14-15, and 37 proceed smoothly to give alpha-glycosides stereoselectively by using a catalytic amount of silyl triflate. This methodology allowed us to achieve syntheses of sulfur-substituted isomaltotetraoside 2 and maltotetraoside 3. These studies also revealed that benzoyl-protected 5-thioglucopyranosyl trichloroacetimidate 12 underwent P-selective glycosylation with C6-OH glucopyranosyl acceptors upon activation by BF3OEt2. This was applied for preparation of sulfur-substituted gentiobiosides 1 and 46. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.028

文献信息

• Application of Site‐Directed Lipase Mutants on Regioselective Acylation of Monosaccharides
  作者：Laura Cipolla、Marina Lotti、Luca De Gioia、Francesco Nicotra

  DOI：10.1081/car-120026464

  日期：2003.12.31

  Mutants F344V and F345V of Candida rugosa lipase1 (CRL1) were tested in acylation reactions of monosaccharide derivatives 1-8, in order to study the regioselectivity, and the substrate specificity of lipase variants towards unnatural substrates, such as carbohydrates. Mutant F344V showed a better reaction kinetics and/or regioselectivity then the wild type enzyme with several substrates while mutant F345V was inefficient in most cases. With the aim of correlating experimental data with the structural features of the enzyme and substrates, the interaction of substrates methyl 4,6-O-benzylidene-alpha-D-glucopyranoside (5a) and 4,6-O-benzylidene-alpha-D-galactopyranoside (6a) with the wild type enzyme and the mutant F344V was investigated, using a molecular modelling approach.
• Synthetic studies on oligosaccharides composed of 5-thioglucopyranose units
  作者：Yasuharu Morii、Hiroko Matsuda、Keiichiro Ohara、Masaru Hashimoto、Kazuo Miyairi、Toshikatsu Okuno

  DOI：10.1016/j.bmc.2005.05.028

  日期：2005.9

  Glycosylation reactions of 5-thioglucopyranosyl trichloroacetimidates bearing ethereal protective groups at the 2-O-position 14-15, and 37 proceed smoothly to give alpha-glycosides stereoselectively by using a catalytic amount of silyl triflate. This methodology allowed us to achieve syntheses of sulfur-substituted isomaltotetraoside 2 and maltotetraoside 3. These studies also revealed that benzoyl-protected 5-thioglucopyranosyl trichloroacetimidate 12 underwent P-selective glycosylation with C6-OH glucopyranosyl acceptors upon activation by BF3OEt2. This was applied for preparation of sulfur-substituted gentiobiosides 1 and 46. (c) 2005 Elsevier Ltd. All rights reserved.