4-methoxyphenyl 6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-β-D-galactopyranoside | 1256157-16-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-β-D-galactopyranoside
• CAS: 1256157-16-0
• 化学式: C₂₂H₃₆O₇Si
• 分子量: 440.609
• InChiKey: DXCKISXMTPVZIR-OUUBHVDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-β-D-galactopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 4-methoxyphenyl 2-O-levulinoyl-3,4,6-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a new glycosphingolipid, neurosporaside, from Neurospora crassa

  摘要：

  The glycosphingolipid neurosporaside (alpha-D-Glcp-(1 -> 2)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 ->)-Cer) occurs in Neurospora crassa. We attempted to synthesize neurosporaside by block synthesis (route A) and linear synthesis (route B). Oligosaccharide derivatives were synthesized using trimethylsilyltrifluoromethanesulfonate and N-iodosuccinimide/trifluoromethane sulfonic acid as promoters. The target tetrasaccharide could not be attained via route A, but route B showed potential: glycosidic bonds (beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp) were formed stereoselectively, leading to the synthesis of glycosphingolipid 2. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.11.018
• 作为产物：
  描述：

  4-甲氧基苯基-Β-D-半乳糖苷 在 吡啶 、 camphor-10-sulfonic acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-methoxyphenyl 6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a new glycosphingolipid, neurosporaside, from Neurospora crassa

  摘要：

  The glycosphingolipid neurosporaside (alpha-D-Glcp-(1 -> 2)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 ->)-Cer) occurs in Neurospora crassa. We attempted to synthesize neurosporaside by block synthesis (route A) and linear synthesis (route B). Oligosaccharide derivatives were synthesized using trimethylsilyltrifluoromethanesulfonate and N-iodosuccinimide/trifluoromethane sulfonic acid as promoters. The target tetrasaccharide could not be attained via route A, but route B showed potential: glycosidic bonds (beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp) were formed stereoselectively, leading to the synthesis of glycosphingolipid 2. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.11.018

文献信息

• Synthesis of the pentasaccharide repeating unit of Escherichia coli O128 antigen
  作者：Xun Lv、Shuihong Cheng、Guoha Wei、Yuguo Du

  DOI：10.1016/j.carres.2010.07.025

  日期：2010.10

  A pentasaccharide, 4-methoxyphenyl 2-acetamido-2-deoxy-beta-D-galactoPyranosyl-(1 -> 4)-alpha-D-galactopyranosyl-(1 -> 3)-2-acetamido-2-deoxy-beta-D-galactoPyranosyl-(1 -> 6)-[alpha-L-fucopyranosyl-(1 -> 2)]-beta-D-galactopyranoside (1), representing the repeating unit of Escherichia coli O128 antigen, was successfully prepared in 23% overall yield via a convergent '2+3' glycosylation strategy. (C) 2010 Elsevier Ltd. All rights reserved.