2-propenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside | 63064-48-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-propenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside
• 英文别名: allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside；allyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranoside；(2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(allyloxy)tetrahydro-2H-pyran-3,4-diyl diacetate；[(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-prop-2-enoxyoxan-2-yl]methyl acetate
• CAS: 63064-48-2
• 化学式: C₁₇H₂₅NO₉
• 分子量: 387.387
• InChiKey: PRSVMSRDBOXABR-HHARLNAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  2-propenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside 在 吡啶 、 sodium azide 、 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 barium hydroxide octahydrate 、 potassium tert-butylate 、 barium(II) oxide 、 三甲基膦 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 11.0h， 生成
  参考文献：
  名称：

  2-乙酰胺基-2-脱氧-1-亚氨基糖C-烷基和C-芳基糖苷：合成和糖苷酶抑制

  摘要：

  施陶丁格/ azawittig /格利雅/环收缩序列应用于两个d -glycopyranose衍生物轴承在C-2位乙酰氨基和叠氮基的C-6位置允许访问前所未有六元升-iminosugars Ç - GlcNAc和ManNAc模拟糖苷。格利雅（Grignard）添加物具有较高的1,2-反式非对映选择性，这强烈暗示了NHAc基团的对映体辅助作用。

  DOI：

  10.1002/ejoc.201800678
• 作为产物：
  描述：

  在 三氟甲磺酸三甲基硅酯 、 双氧水 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-propenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  New α-selective thermal glycosylation of acetyl-protected 2-acetamido-2-deoxy-β-d-glucopyranosyl diphenylphosphinate

  摘要：

  This paper describes new alpha-selective thermal glycosylation using acetyl-protected 2-acetamido-2-deoxy-beta-D-glucopyranosyl diphenylphosphinate (4) as a glycosyl donor. When the glycosylation of 4 with 1-hexanol was carried out under Various conditions, the conditions using trimethylsilyl trifluoromethanesulfonate as a promoter in nitromethane at reflux temperature were most suitable for the formation of the alpha anomer. The glycosylation of 4 with the other common alcohols gave corresponding alpha-glycosides in relatively high yields under the conditions. When cholesterol, a very steric hindered alcohol, was used as a glycosyl acceptor, alpha-glycoside was also produced predominantly. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00069-0

文献信息

• Synthesis of Benzaldehyde-Functionalized Glycans: A Novel Approach Towards Glyco-SAMs as a Tool for Surface Plasmon Resonance Studies
  作者：Sebastian Kopitzki、Knud J. Jensen、Joachim Thiem

  DOI：10.1002/chem.200902693

  日期：——

  In recent years the interest in tools for investigating carbohydrate–protein (CPI) and carbohydrate‐carbohydrate interactions (CCI) has increased significantly. For the investigation of CPI and CCI, several techniques employing different linking methods are available. Surface plasmon resonance (SPR) imaging is a most appropriate tool for analyzing the formation of self‐assembled monolayers (SAM) of

  近年来，人们对研究碳水化合物-蛋白质（CPI）和碳水化合物-碳水化合物相互作用（CCI）的工具的兴趣大大增加。为了调查CPI和CCI，可以使用几种采用不同链接方法的技术。表面等离振子共振（SPR）成像是分析碳水化合物衍生物可模仿糖萼的自组装单分子膜（SAM）形成的最合适工具。与先前用于分析CPI和CCI的SPR成像方法相反，本文报道的新颖方法可轻松，快速地合成接头间隔子和碳水化合物衍生物，并通过控制配体的数量和方向来增强结合作用。为了通过还原胺化固定在具有生物排斥性的氨基官能化SPR芯片上，已通过包括烯烃复分解在内的几个简便步骤合成了多种醛官能化的聚糖结构（葡萄糖，半乳糖，甘露糖，葡糖胺，纤维二糖，乳糖和乳糖胺）。提出了针对凝集素伴刀豆球蛋白A的有效固定方法和首次结合研究。
• A Radical Bidirectional Fragment Coupling Route to Unsymmetrical Ketones
  作者：Lucile Anthore-Dalion、Qiang Liu、Samir Z. Zard

  DOI：10.1021/jacs.6b05344

  日期：2016.7.13

  A powerful strategy for the regioselective bidirectional synthesis of unsymmetrically substituted ketones is described, relying on the fact that the exchange of a xanthate is much faster than the radical addition to an unactivated alkene. The use of an alkene as the formal "alkylating" agent associated with the tolerance for numerous functional groups and the mildness of the experimental conditions

  描述了不对称取代酮的区域选择性双向合成的强大策略，依赖于黄药的交换比未活化烯烃的自由基加成快得多的事实。使用烯烃作为正式的“烷基化”剂，与许多官能团的耐受性和实验条件的温和性相关，消除了与经典离子和过渡金属方法相关的许多问题。
• Compounds that bind to the interferon-gamma, preparation method thereof and medicaments containing same
  申请人：Bonnaffe David

  公开号：US20060166927A1

  公开（公告）日：2006-07-27

  Compound capable of binding to gamma-interferon (γ-IFN), chosen from the molecules corresponding to formula (I) below: in which X is a divalent spacer group that is sufficiently long to allow the two oligosaccharide fragments A and B to each bind to one of the peptide sequences 125 to 143 of the C-terminal ends of a γ-interferon (γ-IFN) homodimer, n represents an integer from 0 to 10, and for example equal to 0, 1, 2, 3, 4 or 5, and each R independently represents a hydrogen atom, an SO 3 − group or a phosphate group, on the condition that no SO 3 − group is in the 3-position of the glucosamine units of compound (I). The invention also relates to the process for preparing these compounds, to the complexes formed by these compounds and gamma-interferon, and to the medicaments comprising these compounds or complexes.

  能够与干扰素-γ（γ-IFN）结合的化合物，选自符合以下公式（I）的分子：其中X是一个二价间隔基团，足够长以允许两个寡糖片段A和B各自结合到一个γ-干扰素（γ-IFN）同源二聚体的C端末端的肽序列125至143，n代表从0到10的整数，例如等于0、1、2、3、4或5，并且每个R独立代表一个氢原子、一个SO3−基团或一个磷酸基团，条件是在化合物（I）的葡萄糖胺单元的3位上没有SO3−基团。本发明还涉及制备这些化合物的方法，这些化合物与干扰素-γ形成的复合物，以及包含这些化合物或复合物的药物。
• Chemical synthesis of N-acetylglucosamine derivatives and their use as glycosyl acceptors by the Mesorhizobium loti chitin oligosaccharide synthase NodC
  作者：Eric Kamst、Korien Zegelaar-Jaarsveld、Gijs A. van der Marel、Jacques H. van Boom、Ben J.J. Lugtenberg、Herman P. Spaink

  DOI：10.1016/s0008-6215(99)00190-1

  日期：1999.10

  lipo-chitin oligosaccharide signal molecules (Nod factors) that are essential for the formation of symbiotic organs on the roots of host plants, a process known as nodulation. Biosynthesis of the chitin oligosaccharide moiety in Nod factors is carried out by the rhizobial N-acetylglucosaminyltransferase NodC. The initial acceptor or primer used for the synthesis of chitin oligosaccharides in vivo is

  摘要根瘤菌细菌合成了脂-几丁质寡糖信号分子（Nod因子），这对于在宿主植物根部形成共生器官至关重要，这一过程称为结瘤。Nod因子中的几丁质寡糖部分的生物合成是通过根瘤菌N-乙酰氨基葡萄糖氨基转移酶NodC进行的。用于体内几丁质寡糖合成的初始受体或引物是未知的。为了研究NodC的受体特异性，我们合成了具有不同糖苷配基的N-乙酰氨基葡糖（GlcNAc）衍生物，并使用表达lotorhizobium loti几丁质寡糖合酶NodC的大肠杆菌菌株的膜制剂在体外测试了它们是否为NodC的受体。使用薄层色谱法分析反应产物表明，含有简单烷基链或连接C-1的其他疏水基团的GlcNAc衍生物是NodC的受体。该酶似乎对糖苷配基是β-连接的受体具有特异性。NodC仍将其中GlcNAc的N-乙酰基部分的甲基被烯丙氧基或苄氧基取代的GlcNAc衍生物用作受体。因此，在该位置上的原始甲基对于NodC和GlcNAc之间
• Stereoselectivity control in anomeric O-alkylation. Application to the synthesis of C2 symmetric glycoconjugates
  作者：A. Lubineau、S. Escher、J. Alais、D. Bonnaffé

  DOI：10.1016/s0040-4039(97)00830-7

  日期：1997.6

  Tetrabutylammonium salts strongly influence the stereoselectivity of O-anomeric alkylation and allows to shift from β to α selectivity. Allyl glucosaminide 7 prepared in this way, was used to synthesize the new type of C2 symmetric neoglycoconjugates 1a-c.

  四丁基铵盐强烈影响O-异头烷基化的立体选择性，并允许从β选择性转变为α选择性。以这种方式制备的烯丙基氨基葡萄糖氨基化物7被用于合成新型的C 2对称新糖缀合物1a-c。