1-O-(triphenylmethyl)-1,2-octadecanediol | 88875-77-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-O-(triphenylmethyl)-1,2-octadecanediol
• 英文别名: 2-Octadecanol, 1-(triphenylmethoxy)-；1-trityloxyoctadecan-2-ol
• CAS: 88875-77-8
• 化学式: C₃₇H₅₂O₂
• 分子量: 528.819
• InChiKey: IKQZTDXMTBYIAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  39
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-O-(triphenylmethyl)-1,2-octadecanediol 在 吡啶 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 2-azido-1-O-(triphenylmethyl)octadecanol
  参考文献：
  名称：

  Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice

  摘要：

  Agelasphin-9b, (2S,3S,4R)-1-O-(alpha-D-galactopyranosyl)-16-methyl-2-[N-((R)-2-hydroxytetracosanoyl)-amino]-1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S;4R)-1-O-(alpha-D-galactopyranosyl)2-(N-hexacosanoylamino)-1,3,4-octadecanetriol, was selected as a candidate for clinical application.

  DOI：

  10.1021/jm00012a018
• 作为产物：
  描述：

  1,2-环氧十八烷 在 吡啶 、 硫酸 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 32.0h， 生成 1-O-(triphenylmethyl)-1,2-octadecanediol
  参考文献：
  名称：

  Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice

  摘要：

  Agelasphin-9b, (2S,3S,4R)-1-O-(alpha-D-galactopyranosyl)-16-methyl-2-[N-((R)-2-hydroxytetracosanoyl)-amino]-1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S;4R)-1-O-(alpha-D-galactopyranosyl)2-(N-hexacosanoylamino)-1,3,4-octadecanetriol, was selected as a candidate for clinical application.

  DOI：

  10.1021/jm00012a018

文献信息

• Synthesis of enantiomerically pure 1-O-phosphocholine-2-O-acyl-octadecane and 1-O-phosphocholine-2-N-acyl-octadecane
  作者：Ulrich Massing、Hansjörg Eibl

  DOI：10.1016/0009-3084(94)90032-9

  日期：1994.2

  These are the key intermediates for the synthesis of the phosphatidylcholine- or sphingomyelin-like end products. R- or S-1-O-phosphocholine-2-O-acyl-octadecane is obtained from the tritylated intermediates via benzylation in position 2, acidic detritylation and conversion of the R- or S-1-hydroxy-2-benzyl-octadecanes to the respective phosphocholines via the phosphoethanolamines. Catalytic hydrogenolysis

  这是关于化学合成对映体纯的R-或S-1-O-磷酸胆碱-2-O-酰基十八烷和R-或S-1-O-磷酸胆碱-2-N-酰基十八烷的首次报道。从结构的角度来看，这些磷脂是磷脂酰胆碱和鞘磷脂之间的中间体。这些模型化合物的合成基于R-或S-1.2-O-异亚丙基-丙二醛，用于与十五烷-三苯基膦溴化物进行Wittig反应时的链延长。通过双键的催化加氢和酸性除去异亚丙基保护基，将所得的1.2-O-异亚丙基-十八碳烯-3-en转化为R-或S-1.2-十八碳二烯醇。R-或S-1.2-十八烷二醇的三酰化作用产生一般的中间体R-或S-1-O-三苯甲基-2-羟基-十八烷。这些是合成磷脂酰胆碱或鞘磷脂样终产物的关键中间体。R-或S-1-O-磷酸胆碱-2-O-酰基十八烷是从三苯甲基化的中间体通过位置2处的苄基化，酸性去三苯甲基化和R-或S-1-羟基-2-苄基十八烷的转化制得的通过磷酸乙醇胺与相应的磷酸胆碱反应。苄基的催化氢
• Phospholipid derivatives, and pharmaceutical composition of the same
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04562179A1

  公开（公告）日：1985-12-31

  New phospholipid derivatives represented by the formula: ##STR1## wherein R.sup.1 is alkyl, alkoxy or alkanoylamino; R.sup.2 is lower alkyl, lower alkanesulfonyl or arenesulfonyl; R.sup.3, R.sup.4 and R.sup.5 are each lower alkyl; n is 0 or 1 A is lower alkylene optionally interrupted by a --NHCO-- group; and Q is oxido or lower alkoxy; provided that n is 0 or A is lower alkylene interrupted by a --NHCO-- group, or Q is lower alkoxy, when R.sup.1 is alkoxy and R.sup.2 is lower alkyl; and pharmaceutically acceptable salts thereof, which exhibit antitumor activity.

  新的磷脂衍生物的化学式为：##STR1## 其中，R.sup.1是烷基，烷氧基或烷酰胺基；R.sup.2是低烷基，低烷磺酰基或芳磺酰基；R.sup.3，R.sup.4和R.sup.5分别是低烷基；n为0或1；A是低烷基撤被--NHCO--基所替代的低烷基；Q是氧化物或低烷氧基；但当R.sup.1为烷氧基，R.sup.2为低烷基时，n为0或A为被--NHCO--基所替代的低烷基，或Q为低烷氧基时，则为药学上可接受的盐，具有抗肿瘤活性。
• US4562179A
  申请人：——

  公开号：US4562179A

  公开（公告）日：1985-12-31
• Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice
  作者：Masahiro Morita、Kazuhiro Motoki、Kohji Akimoto、Takenori Natori、Teruyuki Sakai、Eiji Sawa、Kazuo Yamaji、Yasuhiko Koezuka、Eiichi Kobayashi、Hideaki Fukushima

  DOI：10.1021/jm00012a018

  日期：1995.6

  Agelasphin-9b, (2S,3S,4R)-1-O-(alpha-D-galactopyranosyl)-16-methyl-2-[N-((R)-2-hydroxytetracosanoyl)-amino]-1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S;4R)-1-O-(alpha-D-galactopyranosyl)2-(N-hexacosanoylamino)-1,3,4-octadecanetriol, was selected as a candidate for clinical application.