N-[6-Acetamido-2-N-(N-benzyloxycarbonyl)-L-leucyl-2,6-dideoxy-β-D-glucopyranosyl]-N-octadecyldodecanamide | 245050-66-2

• 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: N-[6-Acetamido-2-N-(N-benzyloxycarbonyl)-L-leucyl-2,6-dideoxy-β-D-glucopyranosyl]-N-octadecyldodecanamide
• CAS: 245050-66-2
• 化学式: C₅₂H₉₂N₄O₈
• 分子量: 901.324
• InChiKey: DYVOYQTVLFZXAO-FZPYAWJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.41
• 重原子数：
  64.0
• 可旋转键数：
  37.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  166.53
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-[6-Acetamido-2-N-(N-benzyloxycarbonyl)-L-leucyl-2,6-dideoxy-β-D-glucopyranosyl]-N-octadecyldodecanamide 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以86%的产率得到N-[6-Acetamido-2-N-L-leucyl-2,6-dideoxy-β-D-glucopyranosyl]-N-octadecyldodecanamide
  参考文献：
  名称：

  Synthesis of a Structurally Defined Antigen-Immunostimulant Combination for Use in Cancer Vaccines

  摘要：

  Ganglioside GM(2) expressed on the cell surface of human cancers is a promising target for immunotherapy because GM(2) antibodies are cytotoxic in vitro and GM(2) antibody formation can be induced upon vaccination in cancer patients. We recently reported on the efficient chemical synthesis of GM(2); clinical trials with these synthetic GM(2) conjugated to a purified carrier protein (KLH) are currently under way. In our efforts to generate a totally synthetic GM(2) cancer vaccine, we have now synthesized GM(2) neoglycolipid 1, which consists of the GM(2)-tetrasaccharide epitope that is linked through a spacer to the B-cell stimulatory glycolipid 4. Target compound 1 was constructed from the GM(2) tetrasaccharide donor 2, the 9-hydroxynonanoate 3 spacer, and the 6-amino-6-deoxy derivative (5) of compound 4. Building block 5 was obtained from Z-protected 6-azido-6-deoxy-N-leucyl-glucosamine derivative 12, which was available from glucosamine by two different approaches; the route with the Z-protected derivative of 4 (10) as intermediate gave the best yields, The neoglycolipid 1 reacted with a number of different GM(2)-reactive antibodies. Vaccination of rabbits with 1 resulted in induction of antibodies against GM(2), thus confirming the viability of this novel concept far the construction of a totally synthetic vaccine.

  DOI：

  10.1002/(sici)1521-3765(19990802)5:8<2432::aid-chem2432>3.0.co;2-5
• 作为产物：
  描述：

  1,3,4-Tri-O-acetyl-6-azido-2-N-(N-benzyloxycarbonyl)leucyl-2,6-dideoxy-β-D-glucopyranoside 在 吡啶 、 1,3-丙二硫醇 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 N-[6-Acetamido-2-N-(N-benzyloxycarbonyl)-L-leucyl-2,6-dideoxy-β-D-glucopyranosyl]-N-octadecyldodecanamide
  参考文献：
  名称：

  Synthesis of a Structurally Defined Antigen-Immunostimulant Combination for Use in Cancer Vaccines

  摘要：

  Ganglioside GM(2) expressed on the cell surface of human cancers is a promising target for immunotherapy because GM(2) antibodies are cytotoxic in vitro and GM(2) antibody formation can be induced upon vaccination in cancer patients. We recently reported on the efficient chemical synthesis of GM(2); clinical trials with these synthetic GM(2) conjugated to a purified carrier protein (KLH) are currently under way. In our efforts to generate a totally synthetic GM(2) cancer vaccine, we have now synthesized GM(2) neoglycolipid 1, which consists of the GM(2)-tetrasaccharide epitope that is linked through a spacer to the B-cell stimulatory glycolipid 4. Target compound 1 was constructed from the GM(2) tetrasaccharide donor 2, the 9-hydroxynonanoate 3 spacer, and the 6-amino-6-deoxy derivative (5) of compound 4. Building block 5 was obtained from Z-protected 6-azido-6-deoxy-N-leucyl-glucosamine derivative 12, which was available from glucosamine by two different approaches; the route with the Z-protected derivative of 4 (10) as intermediate gave the best yields, The neoglycolipid 1 reacted with a number of different GM(2)-reactive antibodies. Vaccination of rabbits with 1 resulted in induction of antibodies against GM(2), thus confirming the viability of this novel concept far the construction of a totally synthetic vaccine.

  DOI：

  10.1002/(sici)1521-3765(19990802)5:8<2432::aid-chem2432>3.0.co;2-5