allyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside | 95069-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: allyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside
• 英文别名: N-[(4aR,6S,7R,8R,8aS)-8-hydroxy-2,2-dimethyl-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• CAS: 95069-09-3
• 化学式: C₁₄H₂₃NO₆
• 分子量: 301.34
• InChiKey: IDMODUZZHWSKOL-VEGXAWMVSA-N

物化性质

• 熔点：
  39-41 °C
• 沸点：
  510.0±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside 在 4-二甲氨基吡啶 、 Dowex 50W (H+) 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 [(2R,3S,4R,5R,6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-prop-2-enoxyoxan-4-yl] octadecanoate
  参考文献：
  名称：

  The isolation and synthesis of two novel N-acetyl glucosamine derivatives from Dictyostelium cellular slime molds which exhibit neurite outgrowth activity

  摘要：

  To clarify the diversity of secondary metabolites of Dictyostelium cellular slime molds and explore any biologically active substances which they may hold, constituents of two species were investigated. From a methanol extract or their fruit bodies, two novel acylated amino sugar were isolated, dictyoglucosamine A (1) from D. purpureum and dictyoglucosamine B (2) from D. discoideum. For further analysis, these compounds were then synthesized from N-aceyl-D-glucosamine. Biological evaluation of 1 and 2 shocked the induce neuronal differentiation of rat pheochromocytoma (PC-12) cells. (C) Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00038-2
• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-Alpha-D-吡喃糖 在 三氟化硼乙醚 、 4-甲基苯磺酸吡啶 作用下， 生成 allyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of linked carbohydrates and evaluation of Their binding for 16S RNA by mass spectrometry

  摘要：

  A library of linked molecules were synthesized from the common sugar moieties existing in the natural amino glycosides. These linked molecules were screened against bacterial 16S RNA for their binding affinity using a mass spectrometry-based technology. Some of these compounds exhibited low micromolar affinity and could serve as leads for further development as antibacterial agents. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2003.09.005

文献信息

• Synthetic approach toward antibiotic tunicamycins — VI total synthesis of tunicamycins
  作者：Tetsuo Suami、Hiroaki Sasai、Kazuhiro Matsuno、Nobuo Suzuki、Yoshimasa Fukuda、Osamu Sakanaka

  DOI：10.1016/s0040-4039(01)81486-6

  日期：1984.1

  Tunicamycins and their eight analogs have been synthesized by condensation of a N-acetyl-D-glucosamine derivative and an anomeric chloride of tunicaminyl uracil, followed by deprotections and N-acylation.

  通过将N-乙酰基-D-葡糖胺衍生物和衣氨酰尿嘧啶的异头氯化物缩合，然后脱保护和N-酰化，合成了衣霉素及其八个类似物。
• Degradation of Derivatives of<i>N</i>-Acetyl-<scp>D</scp>-glucosamine by<i>Rhodococcus rhodochrous</i>IFO 15564: Substrate Specificity and Its Application to the Synthesis of Allyl α-<i>N</i>-Acetyl-<scp>D</scp>-glucosaminide
  作者：Atsuhito KUBOKI、Ryosuke KOMIYA、Takahiro SEKIGUCHI、Kenji KATSURAGI、Takeshi SUGAI、Hiromichi OHTA

  DOI：10.1271/bbb.62.1581

  日期：1998.1

  The substrate specificity was studied for the metabolic degradation of N-acetyl-D-glucosamine (GlcNAc) derivatives by Rhodococcus rhodochrous IFO 15564 which possesses N-acetyl-D-glucosamine deacetylase as a key-step enzyme. This microorganism degraded a wide range of substrates with modified N-acyl groups. The metabolizing activity of this strain became low to the substrates substituted at 1,3,4,6-positions

  研究了以Rhodococcus rhodochrous IFO 15564代谢N-乙酰基-D-葡萄糖胺（GlcNAc）衍生物的代谢的底物特异性，IFO 15564具有N-乙酰基-D-葡萄糖胺脱乙酰基酶作为关键步骤酶。该微生物降解了具有修饰的N-酰基的多种底物。该菌株的代谢活性降低到在GlcNAc的1,3,4,6-位置被取代的底物低，建议GlcNAc本身通过开链醛形式代谢。基于这些结果，通过用Jack豆β-N-乙酰基-D-氨基葡萄糖苷酶选择性水解β-端基异构体，开发了从α，β-异头物混合物中分离烯丙基α-N-乙酰基-D-氨基葡萄糖的简化程序。然后用这种微生物降解反应混合物中所得的N-乙酰基-D-葡糖胺。
• Synthesis of Fluoro-containing muramyl dipeptide analogs
  作者：Zheng-Fu Wang、Jie-Cheng Xu

  DOI：10.1016/s0040-4020(98)00738-8

  日期：1998.10

  Twelve Fluoro-containing muramyl dipeptide analogs with perfluoroalkyl at C1 of sugar moiety or C-terminal of peptidyl chain were synthesized.

  合成了十二个在糖基的C1或肽基链的C端具有全氟烷基的含氟的对甲基二肽类似物。
• Synthetic Approach toward Antibiotic Ezomycins. I. Synthesis of 5-Amino-5-deoxyoctofuranose-(1,4) Derivatives by Henry Reaction and Their Stereochemistry
  作者：Osamu Sakanaka、Takashi Ohmori、Shuji Kozaki、Tetsuo Suami、Toshio Ishii、Shigeru Ohba、Yoshihiko Saito

  DOI：10.1246/bcsj.59.1753

  日期：1986.6

  as antibiotics, which consisted of aminoocturonic acid, aminoglucuronic acid and base. As a part of a total synthesis of ezomycins, the title compounds have been synthesized. A KF-catalyzed Henry reaction between a nitropentose and a glyceraldehyde derivative gave a nitro alcohols mixture. Hydrogenation of the intact mixture, followed by N-acetylation afforded three diastereomers. The absolute configurations

  Ezomycins 是在链霉菌属菌种的发酵啤酒中发现的抗生素，由氨基辛醛酸、氨基葡萄糖醛酸和碱组成。作为 ezomycins 全合成的一部分，已合成标题化合物。硝基戊糖和甘油醛衍生物之间的 KF 催化亨利反应得到硝基醇混合物。将完整混合物氢化，然后进行 N-乙酰化，得到三种非对映异构体。新引入的手性中心的绝对构型是通过化学方法和 X 射线晶体结构分析建立的。
• Synthesis of a 2-acetamido-2-deoxy-α-d-galactopyranosyl analogue of tunicamycin
  作者：Kaichiro Kominato、Seiichiro Ogawa、Tetsuo Suami

  DOI：10.1016/0008-6215(88)85106-1

  日期：1988.3