methyl 6-O-[4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-β-L-rhamnopyranosyl]-2,3,4-tri-O-benzyl-α-D-glucopyranoside | 503066-00-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-[4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-β-L-rhamnopyranosyl]-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: [(2S,3S,4R,5R,6S)-6-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-2-methyl-4-phenylmethoxy-5-[2-(trifluoromethyl)phenyl]sulfonyloxyoxan-3-yl] benzoate
• CAS: 503066-00-0
• 化学式: C₅₅H₅₅F₃O₁₃S
• 分子量: 1013.1
• InChiKey: SBLZUAWTERJKET-NTOXPEMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  72
• 可旋转键数：
  22
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  methyl 6-O-[4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-β-L-rhamnopyranosyl]-2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 sodium amalgam 、 异丙醇 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以80%的产率得到methyl 6-O-(3-O-benzyl-β-L-rhamnopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  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：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 phenyl 4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-1-thio-β-L-rhamnopyranoside 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 、 乙腈 为溶剂， 反应 4.0h， 生成 methyl 6-O-[4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-α-L-rhamnopyranosyl]-2,3,4-tri-O-benzyl-α-D-glucopyranoside 、 methyl 6-O-[4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-β-L-rhamnopyranosyl]-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  On the nitrile effect in l-rhamnopyranosylation

  摘要：

  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.

  DOI：

  10.1016/j.carres.2006.03.036

文献信息

• 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.
• 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.