(2S,3R,4E)-2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl-(1'→1)-2-(hexadecaneoylamido)-3-benzoyloxy-octadec-4-ene-1-ol | 914803-37-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: (2S,3R,4E)-2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl-(1'→1)-2-(hexadecaneoylamido)-3-benzoyloxy-octadec-4-ene-1-ol
• 英文别名: (2S,3R,4E)-2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol
• CAS: 914803-37-5
• 化学式: C₅₃H₈₇NO₁₁
• 分子量: 914.274
• InChiKey: ZHYQAZODVBZNMV-KFOVMZFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.99
• 重原子数：
  65.0
• 可旋转键数：
  37.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  152.76
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4E)-2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl-(1'→1)-2-(hexadecaneoylamido)-3-benzoyloxy-octadec-4-ene-1-ol 在 甲醇 、 sodium 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以93%的产率得到(2S,3R,4E)-α-L-rhamnopyranosyl-(1'->1)-2-(hexadecanoylamido)-4-octadecene-1,3-diol
  参考文献：
  名称：

  Synthesis of α-l-rhamnosyl ceramide and evaluation of its binding with anti-rhamnose antibodies

  摘要：

  An α-L-rhamnosyl ceramide (1, α-L-RhaCer) has been prepared that was recognized by anti-L-rhamnose (anti-Rha) antibodies. During these studies we explored the use of an α-L-rhamnosyl thioglycoside and a trichloroacetimidate as a glycosyl donors. Subsequently, the acceptors desired for glycosylation, 3-O-benzoylazidosphingosine or 3-O-alloxycarbonylsphingosine, were prepared from D-xylose. The thioglycoside donor, 2,3,4-tri-O-acetyl-1-(4-tolyl)thio-α-L-rhamnopyranoside, and the trichloroacetimidate donor, 2,3,4-tri-O-acetyl-1-(2,2,2-trichloroethanimidate)-α-L-rhamnopyranoside, were synthesized in 50% and 78% yield overall, respectively. The synthesis of the glycosylation acceptor employed an addition-fragmentation olefination that was successfully carried out in 53% yield. With the successful synthesis of key intermediates, α-L-RhaCer (1) was prepared without any insurmountable obstacles. Anti-Rha antibodies were prepared in BALB/c mice by immunizing them with rhamnose-ovalbumin (Rha-Ova) with Sigma Adjuvant System (SAS) and the anti-L-Rha antibodies were isolated from the blood sera. Liposomes and EL4 tumor cells were used as model systems to demonstrate the ability of 1 to insert into a lipid bilayer. The interaction of the liposomes or the EL4 cells with α-L-RhaCer (1) and anti-Rha antibodies were investigated by fluorescence microscopy and flow cytometry, respectively, to confirm the ability of glycolipid 1 to be displayed on the tumor cell surface as well as the ability to be recognized by anti-Rha antibodies.

  DOI：

  10.1016/j.bmc.2014.08.002
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 在 三氟化硼乙醚 、 水 、 乙酸肼 、 1-羟基苯并三唑 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 (2S,3R,4E)-2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl-(1'→1)-2-(hexadecaneoylamido)-3-benzoyloxy-octadec-4-ene-1-ol
  参考文献：
  名称：

  Synthesis of α-l-rhamnosyl ceramide and evaluation of its binding with anti-rhamnose antibodies

  摘要：

  An α-L-rhamnosyl ceramide (1, α-L-RhaCer) has been prepared that was recognized by anti-L-rhamnose (anti-Rha) antibodies. During these studies we explored the use of an α-L-rhamnosyl thioglycoside and a trichloroacetimidate as a glycosyl donors. Subsequently, the acceptors desired for glycosylation, 3-O-benzoylazidosphingosine or 3-O-alloxycarbonylsphingosine, were prepared from D-xylose. The thioglycoside donor, 2,3,4-tri-O-acetyl-1-(4-tolyl)thio-α-L-rhamnopyranoside, and the trichloroacetimidate donor, 2,3,4-tri-O-acetyl-1-(2,2,2-trichloroethanimidate)-α-L-rhamnopyranoside, were synthesized in 50% and 78% yield overall, respectively. The synthesis of the glycosylation acceptor employed an addition-fragmentation olefination that was successfully carried out in 53% yield. With the successful synthesis of key intermediates, α-L-RhaCer (1) was prepared without any insurmountable obstacles. Anti-Rha antibodies were prepared in BALB/c mice by immunizing them with rhamnose-ovalbumin (Rha-Ova) with Sigma Adjuvant System (SAS) and the anti-L-Rha antibodies were isolated from the blood sera. Liposomes and EL4 tumor cells were used as model systems to demonstrate the ability of 1 to insert into a lipid bilayer. The interaction of the liposomes or the EL4 cells with α-L-RhaCer (1) and anti-Rha antibodies were investigated by fluorescence microscopy and flow cytometry, respectively, to confirm the ability of glycolipid 1 to be displayed on the tumor cell surface as well as the ability to be recognized by anti-Rha antibodies.

  DOI：

  10.1016/j.bmc.2014.08.002

文献信息

• Efficient Syntheses of a Series of Glycosphingolipids with 1,2‐<i>trans</i>‐Glycosidic Linkages
  作者：Yunpeng Liu、Ning Ding、Hualing Xiao、Yingxia Li

  DOI：10.1080/07328300600859825

  日期：2006.8

  A series of glycosphingolipids with 1,2-trans-glycosidic linkages were synthesized in the presence of neighboring group participation using trichloroacetimidates as glycosyl donors and an azido-sphingosine as the glycosyl acceptor. During the preparation of the target compounds, it was found that the alpha-L-arabinopyranosyl unit in target 7e and intermediates 7b - 7d existed in the C-1(4) conformation and that the b-L-fucopyranosyl unit in 10e adopted the C-4(1) conformation.