N-[2-N-(N-Benzyloxycarbonyl)-L-leucyl-2,6-dideoxy-β-D-glucopyranosyl]-N-octadecyldodecanamide | 113483-71-9

• 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-[2-N-(N-Benzyloxycarbonyl)-L-leucyl-2,6-dideoxy-β-D-glucopyranosyl]-N-octadecyldodecanamide
• 英文别名: N-(2-(N-benzyloxycarbonyl-L-leucyl)amino-2-deoxy-β-D-glucopyranosyl)-N-octadecyldodecanamide；N-(2-(N-benzyloxycarbonyl-L-leucinamido)-2-deoxy-β-D-glucopyranosyl)-N-octadecyl-dodecanoamide；benzyl N-[(2S)-1-[[(2R,3R,4R,5S,6R)-2-[dodecanoyl(octadecyl)amino]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate
• CAS: 113483-71-9
• 化学式: C₅₀H₈₉N₃O₈
• 分子量: 860.272
• InChiKey: XWNNPGHXBRACID-NDYMNTALSA-N

物化性质

• 沸点：
  938.3±65.0 °C(predicted)
• 密度：
  1.07±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  61
• 可旋转键数：
  37
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  158
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-[2-N-(N-Benzyloxycarbonyl)-L-leucyl-2,6-dideoxy-β-D-glucopyranosyl]-N-octadecyldodecanamide 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以90.3%的产率得到N-(2-deoxy-2-L-leucylamino-β-D-glucopyranosyl)-N-octadecyldodecanoylamide
  参考文献：
  名称：

  Syntheses of Peptidoglycolipid Analogs with Distinct Immunomodulating Activities

  摘要：

  Amphiphilic 2-amino-2-deoxy-beta-D-glucopyranosylamides were synthesized from N-protected glucosamine derivatives via N-glycosidation with fatty amines, subsequent N-acylation with fatty acid derivatives and deprotection. They could further be modified with amino acids to give peptido-glycopyranosyl amides, some of which exhibited strong immunostimulatory (BAY Q8939, 8) or immunoadjuvant (BAY R1005, 9) activities.

  DOI：

  10.1080/07328300008544102
• 作为产物：
  描述：

  ethyl dodecanoyl carbonate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 N-[2-N-(N-Benzyloxycarbonyl)-L-leucyl-2,6-dideoxy-β-D-glucopyranosyl]-N-octadecyldodecanamide
  参考文献：
  名称：

  Syntheses of Peptidoglycolipid Analogs with Distinct Immunomodulating Activities

  摘要：

  Amphiphilic 2-amino-2-deoxy-beta-D-glucopyranosylamides were synthesized from N-protected glucosamine derivatives via N-glycosidation with fatty amines, subsequent N-acylation with fatty acid derivatives and deprotection. They could further be modified with amino acids to give peptido-glycopyranosyl amides, some of which exhibited strong immunostimulatory (BAY Q8939, 8) or immunoadjuvant (BAY R1005, 9) activities.

  DOI：

  10.1080/07328300008544102

文献信息

• Synthesis of a Structurally Defined Antigen-Immunostimulant Combination for Use in Cancer Vaccines
  作者：Wulf Dullenkopf、Gerd Ritter、Sheila R. Fortunato、Lloyd J. Old、Richard R. Schmidt

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

  日期：1999.8.2

  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.
• N-(2-Aminoacylamido-2-desoxy-hexosyl)-amide, -carbamate und -harnstoffe, Verfahren zu ihrer Herstellung sowie ihre Verwendung in Arzneimitteln
  申请人：BAYER AG

  公开号：EP0206037B1

  公开（公告）日：1992-01-15
• US4855283A
  申请人：——

  公开号：US4855283A

  公开（公告）日：1989-08-08
• Syntheses of Peptidoglycolipid Analogs with Distinct Immunomodulating Activities
  作者：Oswald Lockhoff、Yutaka Hayauchi

  DOI：10.1080/07328300008544102

  日期：2000.1

  Amphiphilic 2-amino-2-deoxy-beta-D-glucopyranosylamides were synthesized from N-protected glucosamine derivatives via N-glycosidation with fatty amines, subsequent N-acylation with fatty acid derivatives and deprotection. They could further be modified with amino acids to give peptido-glycopyranosyl amides, some of which exhibited strong immunostimulatory (BAY Q8939, 8) or immunoadjuvant (BAY R1005, 9) activities.