methyl 4-O-[(4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-α-L-rhamnopyranosyl)]-2,3-O-isopropylidene-α-L-rhamnopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-[(4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-α-L-rhamnopyranosyl)]-2,3-O-isopropylidene-α-L-rhamnopyranoside
• 英文别名: methyl 4-O-[4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-α-L-rhamnopyranosyl]-2,3-O-isopropylidene-α-L-rhamnopyranoside；[(2S,3S,4R,5R,6S)-6-[[(3aR,4R,6S,7S,7aR)-4-methoxy-2,2,6-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy]-2-methyl-4-phenylmethoxy-5-[2-(trifluoromethyl)phenyl]sulfonyloxyoxan-3-yl] benzoate
• 化学式: C₃₇H₄₁F₃O₁₂S
• 分子量: 766.787
• InChiKey: HJJYAWBMAAGDHU-HQWVTCAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  53
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 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 、 1-(苯基亚硫酰基)哌啶 、 potassium iodide 、 silver(l) oxide 、 2,4,6-三叔丁基嘧啶 作用下， 以 二氯甲烷 为溶剂， 反应 44.5h， 生成 methyl 4-O-[(4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-α-L-rhamnopyranosyl)]-2,3-O-isopropylidene-α-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.
• Direct Synthesis of the β-<scp>l</scp>-Rhamnopyranosides
  作者：David Crich、John Picione

  DOI：10.1021/ol0340890

  日期：2003.3.1

  [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.