prenyl β-D-galactopyranoside | 1300738-19-5

• 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: prenyl β-D-galactopyranoside
• CAS: 1300738-19-5
• 化学式: C₁₁H₂₀O₆
• 分子量: 248.276
• InChiKey: GQJQCKUJCHMTNF-ZKKRXERASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.23
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  99.38
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  prenyl β-D-galactopyranoside 、 苯甲醛二甲缩醛 在 camphor-10-sulfonic acid 、 三乙胺 作用下， 以 乙腈 为溶剂， 以86%的产率得到3-methyl-2-butenyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Alkenyl β-d-galactopyranoside derivatives as efficient chiral templates in stereoselective cyclopropanation and epoxidation reactions

  摘要：

  The synthesis of a wide range of alkenyl 4,6-O-(S)-benzylidene-beta-D-galactopyranosides is described. The cyclopropanation and epoxidation reactions of these compounds were developed. Cyclopropanation reactions took place with high stereoselectivity giving diastereomeric excesses of up to 100%. As a part Of Our aim in studying hydroxyl-directed reactions, their epoxidation with m-CPBA was carried out High diastereomeric excesses (80-100%) were obtained when the hydroxyl group at C-2 of the auxiliary was unprotected The beta-D-galactopyranoside moiety constitutes as an interesting auxiliary, due to its efficient chirality transfer capability as well as providing a way to obtain a variety of glycolipid derivatives (c) 2009 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.003
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 prenyl β-D-galactopyranoside
  参考文献：
  名称：

  Alkenyl β-d-galactopyranoside derivatives as efficient chiral templates in stereoselective cyclopropanation and epoxidation reactions

  摘要：

  The synthesis of a wide range of alkenyl 4,6-O-(S)-benzylidene-beta-D-galactopyranosides is described. The cyclopropanation and epoxidation reactions of these compounds were developed. Cyclopropanation reactions took place with high stereoselectivity giving diastereomeric excesses of up to 100%. As a part Of Our aim in studying hydroxyl-directed reactions, their epoxidation with m-CPBA was carried out High diastereomeric excesses (80-100%) were obtained when the hydroxyl group at C-2 of the auxiliary was unprotected The beta-D-galactopyranoside moiety constitutes as an interesting auxiliary, due to its efficient chirality transfer capability as well as providing a way to obtain a variety of glycolipid derivatives (c) 2009 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.003

文献信息

• Semisynthesis of fuscoside B analogues and eunicosides, and analysis of anti-inflammatory activity
  作者：Douglas H. Marchbank、Russell G. Kerr

  DOI：10.1016/j.tet.2011.03.006

  日期：2011.4

  A small library of semisynthetic analogues of fuscol and eunicol have been prepared and evaluated for in vivo topical anti-inflammatory activity using the mouse-ear edema assay. The first glycosylation of fuscol and eunicol has been achieved using a modified Koenigs-Knorr glycosylation to synthesize new fuscosides and eunicosides, a novel structural class of diterpene glycosides. The availability of adequate glycosylation methods for this synthesis was limited owing to the instability of the glycosyl acceptors. Glycosyl donor protecting group type had a pronounced effect on overall glycosylation yields of a model glycosyl acceptor. This synthesis provided access to the unnatural beta-glycosides allowing for an evaluation of the effect of differing anomeric stereochemistry on anti-inflammatory activity. The PEGylated derivatives of fuscol and eunicol were also synthesized by a convenient acid-promoted solvolysis of the natural product aglycones. This work highlights the importance of the glycan portion of fuscoside B. notably the stereochemical configuration of the glycosidic linkage, in the observed anti-inflammatory activity. (C) 2011 Elsevier Ltd. All rights reserved.