2-tetradecylhexadecanoyl chloride | 66880-78-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: 2-tetradecylhexadecanoyl chloride
• CAS: 66880-78-2
• 化学式: C₃₀H₅₉ClO
• 分子量: 471.251
• InChiKey: DERKYPDUCQPVEN-UHFFFAOYSA-N

物化性质

• 沸点：
  513.3±18.0 °C(Predicted)
• 密度：
  0.884±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.5
• 重原子数：
  32
• 可旋转键数：
  27
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-tetradecylhexadecanoyl chloride 在 吡啶 、 氯磺酸 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 Sulfuric acid mono-[2-(2-tetradecyl-hexadecanoylamino)-ethyl] ester
  参考文献：
  名称：

  Studies on scavenger receptor inhibitors. Part 1: synthesis and structure–activity relationships of novel derivatives of sulfatides

  摘要：

  Scavenger receptors have been proven to be implicated in the formation of atherosclerotic lesions. A series of novel derivatives of sulfatides were synthesized, and their inhibitory activities against incorporation of Dil-acetyl-LDL into macrophages were evaluated in order to clarify the structure-activity relationships of sulfatides as a scavenger receptor inhibitor and find out novel inhibitors with synthetic easiness. The chemical modification of the substructures of sulfatides led to the establishment of the following structure-activity relationships (1) the ceramide moiety can be replaced with another structure bearing two long chains, (2) the galactose moiety can be replaced with another structure or be deleted without a large decrease in the inhibitory activity, (3) the sulfate moiety was crucial, and it was the most preferable functional group for a potent inhibitory activity. The inhibitory activity of (S)-2-octadecanoylamino-2-tetradecylcarbamoyl)ethyl sulfate sodium salt (3a) against incorporation of Dil-acetyl-LDL into macrophages was proven to be based on the inhibition against the binding of acetyl-LDL to the surface of macrophages. We discovered novel scavenger receptor inhibitors with synthetic easiness, such as (S)-2-octadecanoylamino-2-(tetradccylcarbamoyl)ethyl sulfate sodium salt (3a) and 2-octadecanoylamino-1-(octadecanoylaminomethyl)ethyl sulfate sodium salt (13q). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00120-7
• 作为产物：
  描述：

  2-十四烷基棕榈酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以97%的产率得到2-tetradecylhexadecanoyl chloride
  参考文献：
  名称：

  [EN] AMINOOXYLIPIDS FOR THE CONSTRUCTION OF SELF-ASSEMBLING LIPOSOMAL SYSTEMS ENABLING THEIR SUBSEQUENT MODIFICATION BY BIOLOGICALLY FUNCTIONAL MOLECULES
  [FR] AMINOOXYLIPIDES POUR LA CONSTRUCTION DE SYSTÈMES LIPOSOMIQUES À AUTO-ASSEMBLAGE PERMETTANT LEUR MODIFICATION ULTÉRIEURE PAR DES MOLÉCULES BIOLOGIQUEMENT FONCTIONNELLES

  摘要：

  通用公式（I）的新氨氧脂类化合物，其中n1 = 5-30，X是通用公式（II）的聚甲烯链连接物，其中n2 = 2-10，或者X是通用公式（III）的聚乙二醇链连接物，其中n3 = 1-14。提供了一种制备通用公式（I）氨氧脂类化合物的方法，其特征在于将N-叔丁氧羰基-聚甲烯二胺{(CH3)3C-0-(C=0)-HN-(CH2)n-N H2，n = 2-13}或N-叔丁氧羰基-聚乙二醇二胺{(CH3)3C-0-(C=0)-HN-(CH2)2-[0-(CH2)]n-0-(CH2)2NH2，n = 1-14}与通用公式（IV）的对称分支脂肪酸在存在缩合试剂的情况下酰化，其中n1 = 5-30，或者从通用公式（IV）衍生的酰氯化物的酸（V）中的酸（V）的衍生物与缩合试剂一起，其中n1 = 5-30，产生通用公式（VI）的N-Boc-氨基脂类，其中n1 = 5-30，X是通用公式（II）的聚甲烯链连接物或X是通用公式（III）的聚乙二醇链连接物。这些通过去叔丁氧基化转化为通用公式（VII）的氨基脂类，其中n1 = 5-30，X是通用公式（II）的聚甲烯链连接物或X是通用公式（III）的聚乙二醇链连接物。通过它们与N-叔丁氧羰基-氨氧基乙酸在存在缩合试剂的情况下缩合，得到通用公式（VIII）的N-Boc-氨氧脂类，其中n1 = 5-30，X是通用公式（II）的聚甲烯链连接物或X是通用公式（III）的聚乙二醇链连接物，通过去叔丁氧基化得到通用公式（I）的氨氧脂类。通用公式（V）的酰氯化物通过在有机无极性溶剂中与草酸氯化物在存在少量N，N-二甲基甲酰胺的情况下反应制备。利用通用公式I的无毒氨氧脂类化合物构建无毒的自组装脂质体载体，呈现氨氧基团，并使用肟连接技术（结合物：氨氧基团和醛或酮基团）对这些载体进行所谓的“后脂质体”修饰，以生物功能分子。

  公开号：

  WO2018082723A1

文献信息

• Synthesis of O-[2-acetamido-2-deoxy-6O-stearoyl- and -6-O-(2-tetradecylhexadecanoyl)-β-d-glucopyranosyl]-(1→4)- N-acetylnormuramoyl-l-α-aminobutanoyl-d-isoglutamine, lipophilic disaccharide analogues of MDP
  作者：Miroslav Ledvina、Jan Ježek、David Šaman、Tomáš Vaisar、Věra Hříbalová

  DOI：10.1016/0008-6215(94)84291-4

  日期：1994.1

  Silver triflate-promoted condensation of 3,4,6-tri-O-acetyl-2-deoxy-2- phthalimido-beta-D-glucopyranosyl bromide (1) with benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O- (methoxycarbonyl)methyl-alpha-D-glucopyranoside (4) afforded the key compound, benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O- (methoxy-carbonyl)methyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b eta-D- glucopyranosyl)-alpha-D-glucopyranoside

  12的部分O-酰化和保护基的氢解分别得到6-O-硬脂酰基-和6-O-（2-十四烷基十六烷酰基）-二糖-二肽。据报道在细胞介导的免疫中有热原性和佐剂活性。
• Muramyldipeptide derivatives and process for the preparation thereof
  申请人：Daiichi Seiyaku Co., Ltd.

  公开号：US04101536A1

  公开（公告）日：1978-07-18

  Muramyldipeptide derivatives of the formula: ##STR1## wherein Y represents a mycoloyl group or a synthetic higher acyl group having total carbon number of C30-C90 and having at least a branched chain of long alkyl group on the .alpha.-position thereof, Q represents an -L-alanyl-D-isoglutamine group, a -glycyl-D-isoglutamine group or an -L-seryl-D-isoglutamine group; Salts of such derivatives; the method of preparing such derivatives and their salts; the derivatives and their salts having potent immunoadjuvant activities and antitumor activity and being applicable as the agent for the immunotherapy of cancer for humans and animals.

  Muramyldipeptide衍生物的化学式：##STR1## 其中Y代表一个肌醇基团或具有总碳数为C30-C90的合成高酰基团，并且其上至少有一个长烷基链的支链位于其α-位置，Q代表一个-L-丙氨酰-D-异谷氨酰基团，一个-甘氨酰-D-异谷氨酰基团或一个-L-丝氨酰-D-异谷氨酰基团；这些衍生物的盐；制备这些衍生物及其盐的方法；这些衍生物及其盐具有强大的免疫佐剂活性和抗肿瘤活性，并可用作人类和动物的癌症免疫疗法药物。
• Functional capsule membranes. Part 29. Concanavalin A-induced permeability control of capsule membranes corked with synthetic glycolipid bilayers or grafted with synthetic glycopolymers
  作者：Yoshio Okahata、Gen-ichi Nakamura、Hiroshi Noguchi

  DOI：10.1039/p29870001317

  日期：——

  ultrathin nylon capsule membranes were corked with synthetic glycolipid (2C14-glu and 2C14-gal) or grafted with synthetic polymers having pendant saccharides (Poly-glu and Poly-gal). The permeability of NaCl from the capsule corked with glycolipid bilayers having the α-D-glucopyranosyl head group, but not the β-D-galactopyranosyl head group, was increased by interaction with concanavalin A (Con A) because

  用合成的糖脂（2C 14 -glu和2C 14 -gal）对大型超薄尼龙胶囊膜塞塞，或用具有侧链糖的合成聚合物（Poly-glu和Poly-gal）接枝。通过与伴刀豆球蛋白A（Con A）相互作用，可增加与具有α- D-葡萄糖吡喃糖基头基而不是β- D-吡喃半乳糖基头的糖脂双层连接的胶囊中的NaCl的通透性，这是因为连接了双层的扭曲通过Con A与胶囊表面上的α- D-吡喃葡萄糖基头部基团的特异性结合而被诱导。当胶囊接枝具有侧链α- D-吡喃葡萄糖基单元而不是β- D的聚合物时使用-半乳糖吡喃糖基单元，分别通过交替添加Con A和过量的单糖从外部可逆地降低和增加了水溶性染料的渗透性。因此，Con A可以特异性地与α- D形成交联的络合物-葡萄糖吡喃糖基单元在胶囊表面上的接枝聚合物，可能会降低渗透性。加入过量的单糖后，将Con A从胶囊表面去除，并将通透性恢复为原始的快速速率。Con A的这
• COMPOUND
  申请人：Hipler Karsten

  公开号：US20110002983A1

  公开（公告）日：2011-01-06

  The invention provides a compound (which can act as an adjuvant) of Formula I or Formula (II), wherein R 1 R 4 R 5 R 6 and R 7 are each independently selected from hydrogen, acetyl, hydrocarbyl, a lipid moiety and a lipid acyl moiety; R 2 is a hydroxyl, a hydrocarbyl, a lipid moiety, a lipid acyl moiety; or an amino hydrocarbyl group optionally substituted with a hydrocarbyl, a lipid moiety or a lipid acyl moiety; R 3 and R 8 are each independently selected from acetyl, a hydrocarbyl, a lipid moiety and a lipid acyl moiety; X is a peptide chain; The above normuramylglycopeptide compounds can be located in liposomes and micelles and can function as immunomodulators, along with a desired antigen (or DNA encloding the antigen), in (e.g. DNA) vaccines.

  本发明提供了一种化合物（可以作为佐剂），其化学式为I或II式，其中R1R4R5R6和R7各自独立地选择氢、乙酰、烃基、脂质基团和脂肪酰基团；R2为羟基、烃基、脂质基团、脂肪酰基团或者是氨基烃基，该氨基烃基可以选择性地取代烃基、脂质基团或脂肪酰基团；R3和R8各自独立地选择乙酰、烃基、脂质基团和脂肪酰基团；X为肽链。上述诺莫拉葡肽化合物可以位于脂质体和胶束中，并且可以与所需的抗原（或DNA编码抗原）一起在（例如DNA）疫苗中作为免疫调节剂发挥作用。
• Componds derived from normuramyldipeptide
  申请人：IMUTHES LIMITED

  公开号：EP2578598A1

  公开（公告）日：2013-04-10

  The invention provides a compound of Formula I wherein R1, R4 and R5 are each independently selected from hydrogen, acetyl, hydrocarbyl; R2 is a hydrocarbyl, a lipid moiety, a lipid acyl moiety; or an amino hydrocarbyl group optionally substituted with a hydrocarbyl, a lipid moiety or a lipid acyl moiety; R8 is acetyl; X is a peptide chain; wherein hydrocarbyl is preferably acyl or alkyl, which can act as an adjuvant. The above normuramylglycopeptide compounds can be located in liposomes and micelles and can function as immunomodulators, along with a desired antigen or DNA encoding the antigen, in vaccines, e.g., DNA vaccines.

  本发明提供了一种式 I 的化合物 其中 R1、R4 和 R5 各自独立地选自氢、乙酰基、烃基； R2 是烃基、脂质分子、脂质酰基；或任选被烃基、脂质分子或脂质酰基取代的氨基烃基； R8 是乙酰基； X 是肽链； 其中烃基最好是酰基或烷基、 可用作佐剂。 上述常氨酰基糖肽化合物可位于脂质体和胶束中，可与所需抗原或编码抗原的 DNA 一起作为疫苗（如 DNA 疫苗）中的免疫调节剂。