十二烷基-2-乙酰氨基-2-脱氧-β-D-吡喃葡糖苷 | 147025-06-7

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 十二烷基-2-乙酰氨基-2-脱氧-β-D-吡喃葡糖苷
• 中文别名: 十二烷基-2-乙酰氨基-2-脱氧-Β-D-吡喃葡糖苷
• 英文名称: dodecyl 2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: Dodecyl 2-acetamido-2-deoxy-beta-D-glucopyranoside；N-[(2R,3R,4R,5S,6R)-2-dodecoxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 147025-06-7
• 化学式: C₂₀H₃₉NO₆
• 分子量: 389.533
• InChiKey: YNPQAQWLYWACJR-LASHMREHSA-N

物化性质

• 熔点：
  165-167℃

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  十二烷基-2-乙酰氨基-2-脱氧-β-D-吡喃葡糖苷 在 palladium on activated charcoal 吡啶 、 氢氧化钾 、 氢气 、 sodium acetate 、 zinc(II) chloride 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙二醇甲醚 、 水 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 62.0h， 生成 (3aR,4R,6R,7R,7aS)-2-[bis(2-chloroethyl)amino]-4-dodecoxy-6-(hydroxymethyl)-2-oxo-3,3a,4,6,7,7a-hexahydropyrano[3,4-d][1,3,2]oxazaphosphol-7-ol
  参考文献：
  名称：

  糖的烷基化剂。衍生自2-氨基-2-脱氧-d-阿洛糖的环磷酰胺

  摘要：

  摘要通过用相应的2-氨基-2-脱氧-d-阿洛糖衍生物处理相应的2-氨基-2-脱氧-d-阿洛糖衍生物，以良好的收率合成了衍生自烷基2-氨基-4,6-O-亚苄基-2-脱氧-β-d-阿洛吡喃糖苷的环磷酰胺。双（2-氯乙基）磷酰胺二氯化物。成环反应以非常高的非对映选择性发生。随后的氢解得到了衍生自烷基2-氨基-2-脱氧-β-d-allopyranosides的优异的环磷酰胺收率，其亲水性大于前体。起始原料可容易地从2-乙酰氨基-2-脱氧-d-葡萄糖获得。

  DOI：

  10.1016/s0008-6215(98)00056-1
• 作为产物：
  描述：

  十二烷醇 在 4 A molecular sieve 、 sodium methylate 、 氰化汞 作用下， 以 甲醇 、 硝基甲烷 、 甲苯 为溶剂， 反应 30.0h， 生成 十二烷基-2-乙酰氨基-2-脱氧-β-D-吡喃葡糖苷
  参考文献：
  名称：

  糖的烷基化剂。衍生自2-氨基-2-脱氧-d-阿洛糖的环磷酰胺

  摘要：

  摘要通过用相应的2-氨基-2-脱氧-d-阿洛糖衍生物处理相应的2-氨基-2-脱氧-d-阿洛糖衍生物，以良好的收率合成了衍生自烷基2-氨基-4,6-O-亚苄基-2-脱氧-β-d-阿洛吡喃糖苷的环磷酰胺。双（2-氯乙基）磷酰胺二氯化物。成环反应以非常高的非对映选择性发生。随后的氢解得到了衍生自烷基2-氨基-2-脱氧-β-d-allopyranosides的优异的环磷酰胺收率，其亲水性大于前体。起始原料可容易地从2-乙酰氨基-2-脱氧-d-葡萄糖获得。

  DOI：

  10.1016/s0008-6215(98)00056-1

文献信息

• Synthesis and surface-active properties of some alkyl 2-amino-2-deoxy-β-d-glucopyranosides
  作者：Paul Boullanger、Yves Chevalier、Marie-Christine Croizier、Dominique Lafont、Marie-Rose Sancho

  DOI：10.1016/0008-6215(95)00229-1

  日期：1995.11

  Abstract Several alkyl 2-acetamido-2-deoxy-β- d -glucopyranosides were synthesized using either the oxazoline or the N -allyloxycarbonyl procedure. The latter procedure gave better yields with fatty alcohols and cholesterol. The derivatives thus prepared were partly or fully deprotected and their surface-active properties assessed.

  摘要用恶唑啉或N-烯丙氧基羰基合成了2-烷基酰胺基-2-脱氧-β-d-吡喃葡萄糖苷。后一种方法在脂肪醇和胆固醇的作用下具有更好的收率。将由此制备的衍生物部分或完全脱保护，并评估其表面活性。
• Effect of Aglycon Structure on Saccharide Elongation by Cells
  作者：Tamami Kimura、Maria Carmelita Z. Kasuya、Kenichi Hatanaka、Koji Matsuoka

  DOI：10.1002/cbdv.201400278

  日期：2015.2

  Alkyl N‐acetyl‐β‐D‐glucosaminide (GlcNAc primers) with different aglycon moieties were synthesized and used to determine the effect of the aglycon structure on cellular saccharide elongation. Dodecyl N‐acetyl‐β‐D‐glucosaminide (GlcNAc‐C12), tridecan‐7‐yl N‐acetyl‐β‐D‐glucosaminide (GlcNAc‐2C6), and pentacosan‐13‐yl N‐acetyl‐β‐D‐glucosaminide (GlcNAc‐2C12) primers were synthesized by glycosylation of

  合成了具有不同苷元部分的烷基 N-乙酰基-β-D-氨基葡萄糖（GlcNAc 引物），并用于确定苷元结构对细胞糖延伸的影响。十二烷基 N-乙酰基-β-D-氨基葡萄糖 (GlcNAc-C12)、十三烷基-7-基 N-乙酰基-β-D-氨基葡萄糖 (GlcNAc-2C6) 和五十二烷-13-基 N-乙酰基-β-D-氨基葡萄糖 (GlcNAc-2C12) 引物是通过十二聚糖-1-醇、十三聚糖-7-醇和戊聚糖-13-醇分别与过乙酰氨基葡萄糖进行糖基化合成的。将这些引物引入小鼠 B16 黑色素瘤细胞以制备糖脂。孵育 48 小时后，结果表明 GlcNAc-C12 被拉长，得到 NeuAc-Gal-GlcNAc-C12。GlcNAc-2C6 也被拉长得到 Gal-GlcNAc-2C6 和 NeuAc-Gal-GlcNAc-2C6。另一方面，GlcNAc-2C12 引物没有被延长。显着地，
• Stereoselective synthesis of oxiranes as a source of isoserine analogues using d-glucosamine and d-glucose derivatives as chiral templates
  作者：José M. Vega-Pérez、Margarita Vega、Eugenia Blanco、Fernando Iglesias-Guerra

  DOI：10.1016/j.tetasy.2004.09.034

  日期：2004.11

  The synthesis of alkyl (R)-4,6-O-(2,3-epoxypropylidene) hexopyranoside derivatives from N-acetyl-d-glucosamine and d-glucose is described. The reaction of epoxidation with m-CPBA of the corresponding alkenylidene derivatives took place with different stereoselectivities depending upon the substitution of the unsaturated system, the protecting groups of the hydroxyl group at carbon three of the sugar

  描述了由N-乙酰基-d-葡糖胺和d-葡萄糖合成烷基（R）-4，6- O-（2，3-环氧丙叉基）己吡喃糖苷衍生物。相应的烯基亚烷基衍生物与m -CPBA的环氧化反应以不同的立体选择性进行，这取决于不饱和体系的取代，糖部分碳三处羟基的保护基团及其构型。这些环氧乙烷与氮亲核试剂的开环反应得到苯基异丝氨酸前体。
• Glycosylation of dodecyl 2-acetamido-2-deoxy-β-d-glucopyranoside and dodecyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside as saccharide primers in cells
  作者：Toshinori Sato、Minako Takashiba、Rumi Hayashi、Xingyu Zhu、Tatsuya Yamagata

  DOI：10.1016/j.carres.2008.01.022

  日期：2008.4

  Syntheses of oligosaccharides expressed on cells are indispensable for the improvement of the functional analyses of the oligosaccharides and their applications. We are developing saccharide primers for synthesizing oligosaccharides using living cells. In this study, dodecyl 2-acetamido-2-deoxy-beta-D-glucopyranoside (GlcNAc-C12) and dodecyl beta-D-galactopyranosyl-(1 -> 4)-2-acetamido-2-deoxy-beta-D-glucopyranoside (LacNAc-C12) were examined for their abilities to prime the syntheses of neolacto-series oligosaccharides in HL60 cells. When GlcNAc-C12 was incubated with HL60 cells in serum-free medium for 2 days, 14 kinds of glycosylated products were collected from the culture medium. They were separated by high-performance liquid chromatography. The sequences of the products were determined to be neolacto-series oligosaccharides including Lewis(X), sialyl Lewis(X), polylactosamine, and sialylpolylactosamine by mass spectrometry. GlcNAc-C12 was also glycosylated by B16 cells and gave sialyllactosamine. Furthermore, LacNAc-C12 gave similar glycosylated products to GlcNAc-C12. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and protective anti-infective action of anomeric lipophilic glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine
  作者：A. E. Zemlyakov、V. N. Tsikalova、V. V. Tsikalov、V. Ya. Chirva、E. L. Mulik、O. V. Kalyuzhin

  DOI：10.1134/s1068162006040091

  日期：2006.7

  Anomeric pairs of alpha- and beta-dodecyl, alpha- and beta-(1-pentylhexyl), and alpha- and beta-cyclododecyl glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP) were synthesized. The starting beta-D-glucosaminides were obtained by the oxazoline method, and the corresponding alpha-isomers, by the mercuric iodide-catalyzed glycosylation of alcohols with alpha-glucosaminyl chloride peracetate in nitromethane at -90 degrees C. No reliable differences between the stimulation of mouse resistance to the infection with Staphylococcus aureus (doses of 2, 20, and 200 mu g/mouse) and Escherichia coli (doses of 0.05, 1, and 20 mu g/mouse) with the MDP alpha- and beta-glycosides were found.