乙基-2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-Β-D-吡喃葡萄糖苷 | 76155-50-5

• 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: 乙基-2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-Β-D-吡喃葡萄糖苷
• 中文别名: 乙基2-乙酰氨基-2-脱氧-BETA-D-吡喃葡萄糖苷三乙酸酯
• 英文名称: ethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: ethyl-(tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranoside)；Aethyl-(tri-O-acetyl-2-acetylamino-2-desoxy-β-D-glucopyranosid)；ethyl(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy)β-D-glucopyranoside；Ethyl-2-acetamino-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosid；Ethyl-2-acetamido-3,4,6-tri-O-acetyl-β-D-glucopyranosid；(2R,3S,4R,5R,6R)-5-Acetamido-2-(acetoxymethyl)-6-ethoxytetrahydro-2H-pyran-3,4-diyl diacetate；[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-ethoxyoxan-2-yl]methyl acetate
• CAS: 76155-50-5
• 化学式: C₁₆H₂₅NO₉
• 分子量: 375.376
• InChiKey: POOQFLLMEIHRRF-OXGONZEZSA-N

物化性质

• 熔点：
  191℃
• 沸点：
  525℃
• 密度：
  1.24
• 闪点：
  265℃

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  乙基-2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-Β-D-吡喃葡萄糖苷 在 甲醇 、 氨 作用下， 生成 乙基-2-乙酰氨基-2-脱氧-Β-D-吡喃葡萄糖苷
  参考文献：
  名称：

  958. The preparation and properties of acetochloroglucosamine and its use in the synthesis of 2-acetamido-2-deoxy-β-D-glucosides (N-acetyl-β-D-glucosaminides)

  摘要：

  DOI：

  10.1039/jr9570004754
• 作为产物：
  描述：

  p-methylphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 2,4,6-三叔丁基吡啶 、 三乙酰氧基硼 、 三氟甲磺酸三甲基硅酯 、 氨 、 sodium 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 56.0h， 生成 乙基-2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-Β-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Comparing the use of 2-methylenenapthyl, 4-methoxybenzyl, 3,4-dimethoxybenzyl and 2,4,6-trimethoxybenzyl as N–H protecting groups for p-tolyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-d-glucosides

  摘要：

  A hurdle in glycosylation reactions of 2-acetamido glycosyl donors is the formation of a stable and unreactive oxazoline that decreases the yield of these reactions significantly. As an effort to prevent oxazoline formation during glycosylation reactions, we protected the N-H of the acetamido group within a 2-acetamido-2-deoxy-1-thio-beta-D-glucoside with one of four different protecting groups. These groups were either 2-methylenenapthyl, 4-methoxybenzyl, 3,4-dimethoxybenzyl or 2,4,6-trimethoxybenzyl. The resulting N-alkylacetamides were then used in glycosylation reactions with ethanol as a model acceptor. We observed that the ethyl glycosides obtained in each case were obtained with exclusive 3-selectivity without the formation of oxazoline sideproducts. The resulting products were then used to screen conditions for protecting group removal. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.11.026

文献信息

• N-acetylglucosamine derivatives and use thereof
  申请人：Miura Kyoko

  公开号：US20060020127A1

  公开（公告）日：2006-01-26

  The present invention relates to An N-acetylglucosamine derivative represented by the following formula (1), and a hyaluronic acid production promoting agent containing the same and a skin external preparation containing the same: wherein R 1 is a hydrogen atom or an alkyl group having 2 to 18 carbon atoms; R 2 , R 3 , and R 4 are hydrogen atoms or acyl groups having 2 to 18 carbon atoms and may be all the same or different from others; the steric structure at position 1 may be α or β; provided that R 1 , R 2 , R 3 , and R 4 must not be all hydrogen atoms. It is intended to provide an easily available hyaluronic acid production promoting agent and a skin external preparation whereby the production of hyaluronic acid can be promoted in the skin and thus the skin can be maintained in a vital and moist state so that it is expected that the human skin can be prevented from age.

  本发明涉及一种由以下式（1）表示的N-乙酰葡萄糖氨衍生物，以及含有该衍生物的透明质酸生产促进剂和皮肤外用制剂：其中R1是氢原子或具有2到18个碳原子的烷基；R2、R3和R4是氢原子或具有2到18个碳原子的酰基，可以全部相同或不同；位置1处的立体结构可以是α或β；前提是R1、R2、R3和R4不能全部是氢原子。本发明旨在提供一种容易获得的透明质酸生产促进剂和皮肤外用制剂，从而可以促进皮肤中透明质酸的产生，使皮肤保持活力和湿润状态，从而预防人类皮肤老化。
• N-ACETYGLUCOSAMINE DERIVATIVES AND USE THEREOF
  申请人：MIURA Kyoko

  公开号：US20080293673A1

  公开（公告）日：2008-11-27

  The present invention relates to An N-acetylglucosamine derivative represented by the following formula (1), and a hyaluronic acid production promoting agent containing the same and a skin external preparation containing the same: wherein R 1 is a hydrogen atom or an alkyl group having 2 to 18 carbon atoms; R 2 , R 3 , and R 4 are hydrogen atoms or acyl groups having 2 to 18 carbon atoms and may be all the same or different from others; the steric structure at position 1 may be α or β; provided that R 1 , R 2 , R 3 , and R 4 must not be all hydrogen atoms. It is intended to provide an easily available hyaluronic acid production promoting agent and a skin external preparation whereby the production of hyaluronic acid can be promoted in the skin and thus the skin can be maintained in a vital and moist state so that it is expected that the human skin can be prevented from age.

  本发明涉及以下式（1）所表示的N-乙酰葡萄糖氨衍生物，以及含有该衍生物的透明质酸生产促进剂和皮肤外用制剂：其中，R1是氢原子或具有2至18个碳原子的烷基；R2、R3和R4是氢原子或具有2至18个碳原子的酰基，可以全部相同或不同；位置1的立体结构可以是α或β；前提是R1、R2、R3和R4不能全部是氢原子。旨在提供一种易于获得的透明质酸生产促进剂和皮肤外用制剂，通过促进皮肤中透明质酸的产生，从而使皮肤保持活力和湿润状态，预防人体皮肤老化。
• Discovery of the Chemical Function of Glycosidases:  Design, Synthesis, and Evaluation of Mass-Differentiated Carbohydrate Libraries
  作者：Yang Yu、Kwang-Seuk Ko、Corbin J. Zea、Nicola L. Pohl

  DOI：10.1021/ol049389b

  日期：2004.6.1

  Discovery of the catalytic chemical function of the many putative glycosidases coded in genomes currently relies on individual testing of possible substrates, usually as their p-nitrophenol conjugate. Herein, we present an alternative chemical proteomics approach using a synthetic mass-differentiated heat-stable substrate library with mass spectrometry readout. Library components do not serve as reaction inhibitors and both primary and secondary enzyme substrates can be delineated.
• Micheel; Petersen, Chemische Berichte, 1959, vol. 92, p. 298,300, 302
  作者：Micheel、Petersen

  DOI：——

  日期：——
• Kuhn; Kirschenlohr, Chemische Berichte, 1953, vol. 86, p. 1331
  作者：Kuhn、Kirschenlohr

  DOI：——

  日期：——