4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-(2,3-O-isopropylidene-α-L-rhamnopyranosyl)-β-D-galactopyranoside | 403646-61-7

• 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: 4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-(2,3-O-isopropylidene-α-L-rhamnopyranosyl)-β-D-galactopyranoside
• 英文别名: [(2S,4aR,6R,7R,8S,8aS)-8-[[(3aR,4S,6S,7S,7aR)-7-hydroxy-2,2,6-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]oxy]-6-[4-(4-nitrophenyl)butoxy]-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] 2,2-dimethylpropanoate
• CAS: 403646-61-7
• 化学式: C₃₇H₄₉NO₁₃
• 分子量: 715.795
• InChiKey: RCGAIHLETXIDEH-HBNYWQCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  51
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  166
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  S-phenyl 4,6-O-benzylidene-2,3-di-O-p-methoxybenzyl-1-thia-α-D-mannopyranoside 、 4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-(2,3-O-isopropylidene-α-L-rhamnopyranosyl)-β-D-galactopyranoside 在 1-(苯基亚硫酰基)哌啶 、 三氟甲磺酸酐 、 2,4,6-三叔丁基嘧啶 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-[4-O-(4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranosyl]-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of the Salmonella Type E₁ Core Trisaccharide as a Probe for the Generality of 1-(Benzenesulfinyl)piperidine/Triflic Anhydride Combination for Glycosidic Bond Formation from Thioglycosides

  摘要：

  A synthesis of a chromogenic glycoside of the Salmonella anatum group E-1 core trisaccharide is presented in which all three glycosidic bonds, a 1,2-cis-equatorial, a 1,2-trans-axial, and a 1,2-trans-equatorial linkage representing three of the four main classes of glycosidic bond, are formed with thioglycoside donors activated under a single set of conditions by the combination of 1-(benzenesulfinyl)piperidine and trifluoromethanesulfonic anhydride. 2,3-O-Carbonyl- and 2,3-O-isopropylidene-alpha-L-rhamnopyranosyI thioglycosides are found to be highly alpha-selective rhamnosyl donors under these conditions.

  DOI：

  10.1021/jo0108818
• 作为产物：
  描述：

  phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 在 咪唑 、 1-(苯基亚硫酰基)哌啶 、 三氟甲磺酸酐 、 四丁基氟化铵 、 2,4,6-三叔丁基嘧啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-(2,3-O-isopropylidene-α-L-rhamnopyranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of the Salmonella Type E₁ Core Trisaccharide as a Probe for the Generality of 1-(Benzenesulfinyl)piperidine/Triflic Anhydride Combination for Glycosidic Bond Formation from Thioglycosides

  摘要：

  A synthesis of a chromogenic glycoside of the Salmonella anatum group E-1 core trisaccharide is presented in which all three glycosidic bonds, a 1,2-cis-equatorial, a 1,2-trans-axial, and a 1,2-trans-equatorial linkage representing three of the four main classes of glycosidic bond, are formed with thioglycoside donors activated under a single set of conditions by the combination of 1-(benzenesulfinyl)piperidine and trifluoromethanesulfonic anhydride. 2,3-O-Carbonyl- and 2,3-O-isopropylidene-alpha-L-rhamnopyranosyI thioglycosides are found to be highly alpha-selective rhamnosyl donors under these conditions.

  DOI：

  10.1021/jo0108818

文献信息

• Synthesis of the Salmonella Type E₁ Core Trisaccharide as a Probe for the Generality of 1-(Benzenesulfinyl)piperidine/Triflic Anhydride Combination for Glycosidic Bond Formation from Thioglycosides
  作者：David Crich、Hongmei Li

  DOI：10.1021/jo0108818

  日期：2002.7.1

  A synthesis of a chromogenic glycoside of the Salmonella anatum group E-1 core trisaccharide is presented in which all three glycosidic bonds, a 1,2-cis-equatorial, a 1,2-trans-axial, and a 1,2-trans-equatorial linkage representing three of the four main classes of glycosidic bond, are formed with thioglycoside donors activated under a single set of conditions by the combination of 1-(benzenesulfinyl)piperidine and trifluoromethanesulfonic anhydride. 2,3-O-Carbonyl- and 2,3-O-isopropylidene-alpha-L-rhamnopyranosyI thioglycosides are found to be highly alpha-selective rhamnosyl donors under these conditions.