N-(R)-3-hydroxytetradecanoyloxysuccinimide | 33796-65-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: N-(R)-3-hydroxytetradecanoyloxysuccinimide
• 英文别名: (2,5-dioxopyrrolidin-1-yl) (3R)-3-hydroxytetradecanoate
• CAS: 33796-65-5
• 化学式: C₁₈H₃₁NO₅
• 分子量: 341.448
• InChiKey: XUZQVQPOSKDUDR-OAHLLOKOSA-N

物化性质

• 熔点：
  103-104 °C
• 沸点：
  459.1±47.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(R)-3-hydroxytetradecanoyloxysuccinimide 在 三氯化铁 作用下， 生成 benzyl-2-(D-acetoxytetradecanoylamino)-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  A convenient synthesis of 2-deoxy-2-(d- and -(l-3-hydroxytetradecanoyl-amino)-d-glucose: diastereoisomers of the monomeric, lipid A component of the bacterial Iipopolysaccharide

  摘要：

  DOI：

  10.1016/s0008-6215(00)84616-9
• 作为产物：
  描述：

  (3R,4R,5S,6R)-6-(acetoxymethyl)-3-aminotetrahydro-2H-pyran-2,4,5-triyl triacetate 生成 N-(R)-3-hydroxytetradecanoyloxysuccinimide
  参考文献：
  名称：

  HASEGAWA, AKIRA;KI, SO MAKOTO;UNGER, FRANK MICHAEL

  摘要：

  DOI：

文献信息

• Synthesis and In vitro activities of a spacer-containing glycophospholipid ligand of a lipopolysaccharide receptor involved in endotoxin tolerance
  作者：Daniel Charon、Michelle Mondange、Jean-François Pons、Karine Le Blay、Richard Chaby

  DOI：10.1016/s0968-0896(98)00027-3

  日期：1998.6

  with tetrabenzyl pyrophosphate. Hydrogenation on a Pd on carbon catalyst permitted the isolation of 6-(6-aminohexanoyl)-2,3-dideoxy-2,3-di-[(R)-3-hydroxy-tetradecanamido ] -alpha-D-glucopyranose 1,4-diphosphate (PPDm2-B). In mouse macrophages, PPDm2-B enhanced the lipopolysaccharide (LPS)-dependent secretion of tumor necrosis factor alpha (TNF-alpha), and inhibited the LPS-induced desensitization of these

  由N，N'-酰化和双磷酸化的2,3-二脱氧-2,3-二氨基-D-葡萄糖的衍生物组成的糖脂，在碳6处带有6-氨基己酰基侧链作为间隔臂（PPDm2-B），已经合成了其并评估了其对鼠巨噬细胞的作用。合成从2,3-二氨基-D-葡萄糖开始，这基本上是通过已知程序从葡糖胺获得的，因为尝试使用另一种已知前体（3-硝基糖苷）会导致意想不到的结果。用（D）-3-苄氧基肉豆蔻酸的羟基琥珀酰亚胺酯进行选择性N-酰化，然后通过6-叠氮基丙烯酰氯酯化唯一的伯羟基官能团，并通过用四苄基焦磷酸酯处理将所得的1,4-二醇磷酸化。在碳催化剂上的钯上氢化可分离出6-（6-氨基己基）-2，3-二脱氧-2，3-二-[（R）-3-羟基-十四烷酰胺基]-α-D-吡喃葡萄糖1,4-二磷酸酯（PPDm2-B）。在小鼠巨噬细胞中，PPDm2-B增强了肿瘤坏死因子α（TNF-α）的脂多糖（LPS）依赖性分泌，并抑制了LPS诱导的这些细胞脱敏
• A Synthesis of 2-Substituted 2-Aminoethanol Derivatives Having Inhibitory Activity against Protein Kinase C.
  作者：Tameo IWASAKI、Hiroyoshi YAMAZAKI、Takashi NISHITANI、Kazuhiko KONDO、Tadashi SATO

  DOI：10.1248/cpb.40.122

  日期：——

  A series of 2-aminoethanol derivatives was synthesized and their inhibitory activities against protein kinase C were investigated. Among these compounds, 2-endo-hexadecylamino-5-norbornene-2-exo-methanol (4h) and 2-endo-hexadecylamino-5-norbornene-2, 3-exo-dimethanol (4i) inhibited protein kinase C at the IC50 values of 2×10-5 and 1×10-5 M, respectively, but not protein kinase A at a concentration of 1×10-3 M. The structure-activity relationships are discussed.

  合成了一系列2-氨基乙醇衍生物，并研究了它们对蛋白激酶C的抑制活性。在这些化合物中，2-内源性十六烷基氨基-5-诺尔戊烯-2-外源性甲醇（4h）和2-内源性十六烷基氨基-5-诺尔戊烯-2, 3-外源性二甲醇（4i）分别在2×10^-5 M和1×10^-5 M时抑制蛋白激酶C，但在1×10^-3 M浓度下对蛋白激酶A没有抑制作用。讨论了结构-活性关系。
• The Structure of Viscosin, A Peptide Antibiotic. I. Syntheses of D-and L-3-Hydroxyacyl-L-leucine Hydrazides Related to Viscosin
  作者：MINORU HIRAMOTO、KOZO OKADA、SOTOO NAGAI、HIROSHI KAWAMOTO

  DOI：10.1248/cpb.19.1308

  日期：——

  Sixteen D- and L-3-hydroxyacyl-L-leucine hydrazides related to viscosin have been synthesized. Condensation of DL-3-hydroxy fatty acids with L-leucine methyl ester by the azide method or the active ester method gave DL-3-hydroxyacyl-L-leucine methyl esters, which were then converted to their hydrazides. Each of the racemic hydrazides could readily be resolved into the respective optically active diastereoisomers by means of fractional crystallization using alcohols. All of the D- and L-3-hydroxyacyl-L-leucine hydrazides prepared showed antimicrobial activity against four kinds of microorganisms only comparable to or less than that of the saturated straight chain fatty acids of corresponding carbon numbers.

  已经合成了16种与粘菌素相关的D-和L-3-羟基酰基-L-亮氨酸酰肼。通过叠氮化法或活性酯法将DL-3-羟基脂肪酸与L-亮氨酸甲酯缩合，得到DL-3-羟基酰基-L-亮氨酸甲酯，然后将其转化为酰肼。通过醇类分馏结晶法，每种外消旋酰肼都可以很容易地转化为各自的光学活性非对映异构体。制备的所有D-和L-3-羟基酰基-L-亮氨酸酰肼对四种微生物的抗菌活性仅与相应碳数的饱和直链脂肪酸相当或更低。
• HASEGAWA, AKIRA;KI, SO MAKOTO;UNGER, FRANK MICHAEL
  作者：HASEGAWA, AKIRA、KI, SO MAKOTO、UNGER, FRANK MICHAEL

  DOI：——

  日期：——
• 2,3-DIAMINO-2,3-DIDESOXYHEXOSE DERIVATIVES, PROCESSES FOR THEIR PREPARATION AND THEIR USE
  申请人：SANDOZ AG

  公开号：EP0180608B1

  公开（公告）日：1990-07-25