2-naphthaldehyde di(i-butyl)acetal | 161767-00-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-naphthaldehyde di(i-butyl)acetal
• 英文别名: 2-naphthaldehyde di(isobutyl) acetal；naphthalene-2-formaldehyde diisobutyl acetal；2-[Bis(2-methylpropoxy)methyl]naphthalene
• CAS: 161767-00-6
• 化学式: C₁₉H₂₆O₂
• 分子量: 286.414
• InChiKey: UZYBZWCZBGTSNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-naphthaldehyde di(i-butyl)acetal 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N-碘代丁二酰亚胺 、 lithium aluminium tetrahydride 、 硼烷四氢呋喃络合物 、 草酰氯 、 乙醇 、 三氟甲磺酸三甲基硅酯 、 乙酸肼 、 copper(II) bis(trifluoromethanesulfonate) 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 39.5h， 生成 N-benzyl-N-benzyloxycarbonyl-5-aminopentyl 3-O-benzyl-4-O-(2-naphthyl)methyl-β-D-rhamnopyranoside
  参考文献：
  名称：

  化学合成阐明了自闭症相关细菌克氏梭菌荚膜十八糖的关键抗原表位。

  摘要：

  肠道病原体梭状芽胞杆菌与自闭症谱系障碍（ASD）的发作有关。要创建针对螺栓念珠菌的疫苗，重要的是要确定具有免疫活性的荚膜多糖（CPS）的确切保护表位。在这里，制备了一系列的紫花C. CPS聚糖，直至十八糖。键实现的全合成是[2 + 2]根据一个β-偶联策略d -RHA p - （1→3）-α- d -Man p重复单元，其又被立体选择性β-访问d鼠李糖基化。4,6‐ O亚苄基诱导的构象锁定是形成β- d-甘露糖型糖苷的强大策略。通过Swern氧化和硼氢化物还原有效地实现了基于C2差向异构化的β- d-奎奴诺酮的间接策略。顺序糖基化，区域选择性和整体脱保护产生了二糖和四糖，直至十八糖。对灭活的克雷伯氏菌进行免疫的兔血清的糖微阵列分析显示对二糖和四糖有体液免疫反应，但没有更长的序列。四糖可能是设计抗克氏梭菌的糖结合疫苗的关键主题。

  DOI：

  10.1002/anie.202007209
• 作为产物：
  描述：

  异丁醇 、 2-萘甲醛 在 calcium sulfate 、 D(+)-10-樟脑磺酸 作用下， 反应 48.0h， 以90%的产率得到2-naphthaldehyde di(i-butyl)acetal
  参考文献：
  名称：

  Synthesis of bi-fluorescence-labeled lactoside: A substrate for continual assay of ceramide glycanase

  摘要：

  A bi-fluorescence labeled derivative suitable for analysis of ceramide glycanase activity was constructed from 4-pentenyl lactoside. Selective modification of the galactosyl residue was attained by formation of 4',6'-naphthylmethylidene derivative, which was followed by regioselective reductive ring opening. The aglycon was extended by Michael addition of 2-aminoethanetiol, and dansylated at the terminal amino group. Excitation of the naphthyl group results in emission from the dansyl group, while the emission from the naphthyl group is quenched by the dansyl group. Upon digestion with ceramide glycanase, the energy transfer is severed and a decrease in the dansyl emission concommitant with an increase in the naphthyl emission was observed. This substrate was successfully used to analyze ceramide glycanase activity.

  DOI：

  10.1016/s0957-4166(00)80383-3

文献信息

• 一种革兰氏阳性菌表面荚膜多糖结构衍生物 的制备方法
  申请人：江南大学

  公开号：CN108329362B

  公开（公告）日：2020-10-09

  本发明公开了一种革兰氏阳性菌表面荚膜多糖结构衍生物的制备方法，属于糖化学领域。本发明以葡糖糖为糖基供体，获得目标β‑的糖苷键，然后通过氧化还原的葡萄糖C‑2号位的方法成功合成二糖砌块，接着以该二糖砌块为重复单元合成目标的寡糖结构，例如革兰氏阳性菌细胞壁荚膜多糖结构衍生物[→3)‑α‑D‑Manp‑(1→4)‑β‑D‑Rhap‑(1→]5‑Linker。十糖的还原端接有连接臂用于将来与蛋白质连接制成糖缀合物，用于免疫学研究。本发明提供的方法简单、省时、省力且成本低廉，所得革兰氏阳性菌表面荚膜多糖结构衍生物有可能用作与自闭症相关的医药的开发制备。
• Chemical Synthesis and Antigenicity Evaluation of <i>Shigella dysenteriae</i> Serotype 10 O-Antigen Tetrasaccharide Containing a (<i>S</i>)-4,6-<i>O</i>-Pyruvyl Ketal
  作者：Chunjun Qin、Lingxin Li、Guangzong Tian、Meiru Ding、Shengyong Zhu、Wuqiong Song、Jing Hu、Peter H. Seeberger、Jian Yin

  DOI：10.1021/jacs.2c05953

  日期：2022.11.23

  resistance of this pathogen. The Shigella O-antigen is a promising vaccine target. To identify the immune epitopes of the glycan, the first total synthesis of Shigella dysenteriae serotype 10 O-antigen tetrasaccharide containing a (S)-4,6-O-pyruvyl ketal was completed. The 1,2-trans-β-glycosylation & C2 epimerization and conformational locking strategies facilitated the construction of two 1,2-cis-β-glycosidic

  志贺氏菌是导致儿童急性腹泻的第二大常见病原体。由于这种病原体的耐药性不断增加，人们仍热切期待抗志贺氏菌疫苗的出现。志贺氏菌O抗原是一个很有前途的疫苗靶点。为了鉴定聚糖的免疫表位，首次全合成了含有 ( S )-4,6 - O-丙酮酰缩酮的痢疾杆菌血清型 10 O-抗原四糖。1,2-反式-β-糖基化和 C2 差向异构化和构象锁定策略促进了两个 1,2-顺式的构建-β-糖苷键。通过添加给电子苄基提高了糖基供体和受体的反应性，从而实现了四糖的有效组装。( S )-4,6- O -丙酮酰缩酮由于其对糖基化立体特异性和效率的影响而在最后阶段引入。此外，还合成了 ( R ) -4,6- O-丙酮酸化和非丙酮酸化四糖以及另外三个片段。聚糖微阵列筛选显示四糖重复单元是 O 抗原的关键抗原表位。此外，( S )-4,6- O-丙酮酰缩酮是该抗原的一个基本结构特征，用于设计针对S. dysenteriae血清型
• Simple and conveniently accessible bi-fluorescence-labeled substrates for amylases
  作者：Hiroyuki Oka、Tetsuo Koyama、Ken Hatano、Daiyo Terunuma、Koji Matsuoka

  DOI：10.1016/j.bmcl.2010.01.117

  日期：2010.3

  Synthesis of bi-fluorescence-labeled maltooligosaccharides for amylase assay was accomplished. Preliminary biological evaluation of both bi-fluorescence-labeled maltohexasaccharide and maltose using alpha-amylase was carried out, and the hexaosyl derivative showed unique variation on the basis of fluorescence resonance energy transfer (FRET). (C) 2010 Elsevier Ltd. All rights reserved.
• Synthetic studies of bi-fluorescence-labeled maltooligosaccharides as substrates for α-amylase on the basis of fluorescence resonance energy transfer (FRET)
  作者：Hiroyuki Oka、Tetsuo Koyama、Ken Hatano、Koji Matsuoka

  DOI：10.1016/j.bmc.2011.10.065

  日期：2012.1

  A series of bi-fluorescence-labeled maltooligosaccharides that lead to fluorescence resonance energy transfer (FRET) was systematically synthesized. Effective FRETs were observed with all of the synthesized probes. Digestion of probes having tetra-, quintet-, hexa- or hepta-saccharidic chain lengths with human saliva alpha-amylase resulted in disappearance of FRET when an excitation wavelength of at 290 nm was used followed by detection at ca. 520 nm due to emission from the dansyl moiety. However, continuous FRET was observed when probes having di- or trisaccharidic chain lengths were used as substrates. In addition to the substrate characteristics based on saccharidic chain length, the reaction rates of digestion for the substrates by amylase were different and also depended on their saccharidic chain length. (C) 2011 Elsevier Ltd. All rights reserved.
• A bi-fluorescence-labeled substrate for ceramide glycanase based on fluorescence energy transfer
  作者：Koji Matsuoka、Shin-Ichiro Nishimura、Yuan C. Lee

  DOI：10.1016/0008-6215(95)00238-o

  日期：1995.10

  An alkyl lactoside containing two different fluorescence probes as an energy donor and an energy acceptor was synthesized as a substrate for ceramide glycanase. n-Pentenyl beta-lactoside was converted into its 4',6'-O-(2-naphthylmethylidene) derivative with subsequent benzoylation of all remaining OH groups. The fully protected lactoside was treated with borane-trimethylamine complex and aluminum chloride in tetrahydrofuran [P.J. Garegg, Pure Appl. Chem., 56 (1984) 845-858] for selective opening of the 4',6'-acetal group to give the 6'-O-(2-naphthylmethyl) derivative in high yield, After O-debenzoylation, the omega-alkenyl group at the reducing end was extended by Michael addition with HS(CH2)(2)NH2 . HCl to provide an amino group at the terminal position. The amino group was then dansylated to give the target lactoside, which has two different fluorescent probes at each end, Excitation at 290 nm (of the 2-naphthyl group) of the bi-fluorescence-labeled lactoside showed emissions at 335 nm (2-naphthyl) and at 540 nm (dansyl). The distance between the naphthyl group and the dansyl group was estimated to be 12 Angstrom by the Forster relationship. Digestion of this lactoside with American leech (Macrobdella decora) ceramide glycanase [B. Zhou et al., J. Biol. Chem., 264 (1989) 12,272-12,277] resulted in an increase in the naphthyl emission with a concomitant decrease in the dansyl emission, These changes can be used for continuous monitoring of the ceramide glycanase activity.