phenyl 4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-1-thio-β-L-rhamnopyranoside | 503065-97-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-1-thio-β-L-rhamnopyranoside
• 英文别名: [(2S,3S,4R,5R,6R)-2-methyl-4-phenylmethoxy-6-phenylsulfanyl-5-[2-(trifluoromethyl)phenyl]sulfonyloxyoxan-3-yl] benzoate
• CAS: 503065-97-2
• 化学式: C₃₃H₂₉F₃O₇S₂
• 分子量: 658.716
• InChiKey: AQWCHTORLANVHE-OEZYNDFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  phenyl 4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-1-thio-β-L-rhamnopyranoside 在 sodium amalgam 、 1-(苯基亚硫酰基)哌啶 、 异丙醇 、 2,4,6-三叔丁基嘧啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 76.5h， 生成 1-adamantyl 3-O-benzyl-β-L-rhamnopyranoside
  参考文献：
  名称：

  Direct Synthesis of the β-l-Rhamnopyranosides

  摘要：

  [GRAPHICS]The direct formation Of beta-L-rhamnopyranosides by means of thioglycoside donors protected with a 2-O-sulfonate ester and, ideally, a 4-O-benzoyl ester, is reported. Activation is achieved with the combination of 1-benzenesulfinyl piperidine and triflic anhydride in the presence of 2,4,6-tri-tert-butylpyrimidine. Selectivities vary from moderate to good, and the sulfonyl group is easily removed post-glycosylation with sodium amalgam in 2-propanol.

  DOI：

  10.1021/ol0340890
• 作为产物：
  描述：

  2-三氟甲基苯磺酰氯 在 2,3,5-三甲基吡啶 、 4-二甲氨基吡啶 、 potassium iodide 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成 phenyl 4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-1-thio-β-L-rhamnopyranoside
  参考文献：
  名称：

  Direct Synthesis of the β-l-Rhamnopyranosides

  摘要：

  [GRAPHICS]The direct formation Of beta-L-rhamnopyranosides by means of thioglycoside donors protected with a 2-O-sulfonate ester and, ideally, a 4-O-benzoyl ester, is reported. Activation is achieved with the combination of 1-benzenesulfinyl piperidine and triflic anhydride in the presence of 2,4,6-tri-tert-butylpyrimidine. Selectivities vary from moderate to good, and the sulfonyl group is easily removed post-glycosylation with sodium amalgam in 2-propanol.

  DOI：

  10.1021/ol0340890

文献信息

• On the nitrile effect in l-rhamnopyranosylation
  作者：David Crich、Mitesh Patel

  DOI：10.1016/j.carres.2006.03.036

  日期：2006.7

  It is shown that the use of 5% acetonitrile or propionitrile in dichloromethane functions to increase the beta-selectivity of a number of L-rhamnopyranosylation reactions conducted by the thioglycoside method with activation by the 1-benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride couple. The use of more significant quantities of acetonitrile or propionitrile results in the formation of complex reaction mixtures containing little coupled product, but from which Ritter-type products can be isolated. (c) 2006 Elsevier Ltd. All rights reserved.