β-D-2-deoxy-glucopyranose | 13299-16-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-2-deoxy-glucopyranose
• 英文别名: 2-deoxy-D-glucose；2-deoxyglucose；2-Deoxy-beta-d-arabino-hexopyranose；(2R,4R,5S,6R)-6-(hydroxymethyl)oxane-2,4,5-triol
• CAS: 13299-16-6
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: PMMURAAUARKVCB-KAZBKCHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  β-D-2-deoxy-glucopyranose 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 Octadecanoic acid ((2R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-dodecyl-amide
  参考文献：
  名称：

  Syntheses of glycosylamides as glycolipid analogs

  摘要：

  In search of a simple synthetic access to analogs of naturally occurring glycolipids, glycosylamides have been synthesised in a two-step procedure from unprotected sugars, long-chain amines, and fatty acids. The N-glycosylation proceeded stereospecifically yielding crystalline beta-glycopyranosylamines. C-13 NMR spectroscopy of the glycosylamines in organic solvents revealed partial anomerisation, leading to alpha-glycosylamines and in part to corresponding N-furanosides. Selective N-acylation of either pure beta-glycosylamines or anomeric mixtures thereof with activated fatty acid led to formation of beta-glycosylamides exclusively. As evidenced by NMR spectroscopy, the glycosylamides exhibited rotameric isomerism. The glycosylamides were found to be strong stimulators of the specific immune response against antigens. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00278-x
• 作为产物：
  描述：

  2-deoxy-maltose 生成 β-D-2-deoxy-glucopyranose
  参考文献：
  名称：

  CHIBA, SEIYA;KIMURA, ATSUO, AGR. AND BIOL. CHEM. , 54,(1990) N1, C. 3023-3024

  摘要：

  DOI：

文献信息

• [EN] AMYLOID TARGETING AGENTS AND METHODS OF USING THE SAME<br/>[FR] AGENTS CIBLANT LES AMYLOÏDES ET PROCÉDÉS DE LEUR UTILISATION
  申请人：AMYDIS DIAGNOSTICS

  公开号：WO2015143185A1

  公开（公告）日：2015-09-24

  Provided herein is the design and synthesis of novel molecular rotor fluorophores useful for detection of amyloid or amyloid like proteins. The fluorophores are designed to exhibit enhanced fluorescence emission upon associating with amyloid or amyloid like proteins as compared to unbound compound. Also disclosed herein are the methods for treating of diseases associated with an amyloid or amyloid like proteins.

  本文提供了用于检测淀粉样蛋白或类淀粉样蛋白的新型分子转子荧光团的设计和合成。这些荧光团被设计为与淀粉样蛋白或类淀粉样蛋白结合时，与未结合化合物相比表现出增强的荧光发射。本文还披露了用于治疗与淀粉样蛋白或类淀粉样蛋白相关疾病的方法。
• 31P-N.m.r. spectroscopy in wood chemistry. Phosphite derivatives of carbohydrates
  作者：Yuri Archipov、Dimitris S. Argyropoulos、Henry Bolker、Cyril Heitner

  DOI：10.1016/0008-6215(91)80005-8

  日期：1991.11

  and model compounds for lignin-carbohydrate complexes were reacted with 1,3,2-dioxaphospholanyl chloride, and the 31P-n.m.r. spectra of the derivatives were obtained in order to correlate the signals with the structural details of the compounds. The derivatives of most of the carbohydrates exhibited spectra containing well resolved signals in the range 138-132 p.p.m., and the number of lines accorded

  摘要使选定的无环和环状多元醇，单糖，二糖，高级寡糖和木质素-碳水化合物配合物的模型化合物与1,3,2-二氧杂磷酰氯酰氯反应，得到衍生物的31P-nmr光谱以使它们相互关联。表示化合物的结构细节。大多数碳水化合物的衍生物显示出的光谱包含在138-132 ppm范围内的分辨良好的信号，并且谱线数与相应化合物中的羟基数相符。单糖衍生物中C-1处磷原子的化学位移值是所涉及的端基异构体的特征。由于完全分解的光谱分别具有糖和木质素相关部分的特征信号，获得了相关模型化合物的一部分，该方法似乎非常适合于对木质素-碳水化合物复合物衍生的分子进行结构解析。对环糊精（环麦芽六-，庚-和八糖）进行了衍生化处理，检查后得出的光谱彼此之间存在显着差异。
• Syntheses of β-2-deoxy-D-glycosides assisted by glycosidases
  作者：Jean-Michel Petit、Françoise Paquet、Jean-Marie Beau

  DOI：10.1016/0040-4039(91)80769-3

  日期：1991.10

  Enzyme-catalyzed preparation of β-2-deoxy-D-glucosides and galactosides including disaccharides has been achieved using the corresponding glycals as substrates.

  使用相应的糖基作为底物，已经实现了酶催化的β-2-脱氧-D-葡萄糖苷和半乳糖苷（包括二糖）的制备。
• Quantitative analysis of selective glycosylation of saccharides with aromatic amines
  作者：Toshihiko Hanai、Keiko Shimada、Nobuhiro Koyama、Yukio Nohara

  DOI：10.1016/j.carres.2020.108171

  日期：2020.12

  Glycosylation, a part of the Maillard reaction, occurs non-enzymatically in food and biological processes. The selectivity of N-glycosylation was analyzed based on the reactivity of monosaccharides with aromatic amines, including aromatic amino acids, and the degree of molecular interaction (MI) measured using liquid chromatography. Furthermore, the chemical structures of reaction products were determined

  糖基化是美拉德反应的一部分，在食品和生物过程中以非酶促方式发生。N-糖基化的选择性基于单糖与芳香胺（包括芳香氨基酸）的反应性以及使用液相色谱测量的分子相互作用 (MI) 程度进行分析。此外，使用 X 射线晶体学和/或 NMR 确定反应产物的化学结构。使用不同构象的优化能量值在计算机中估计可能的反应产物。使用模型相的计算机分析计算氨基和糖类的 MI 能量值。具有较大 MI 值的糖类容易产生稳定的 N-糖苷晶体。葡萄糖（一种能量糖）的反应速度很慢，它很容易产生 Amadori 化合物。芳香胺与糖类反应性的研究、单糖在色谱中氨基相保留的测量以及 N-糖苷的合成以确定其结构将为候选药物的修饰提供有关选择性糖基化的有用信息以提高它们的水溶性。
• Solvolyses of 2-Deoxy-α- and β-<scp>d</scp>-Glucopyranosyl 4‘-Bromoisoquinolinium Tetrafluoroborates
  作者：Jiang Zhu、Andrew J. Bennet

  DOI：10.1021/jo0004106

  日期：2000.7.1

  state charge delocalization onto the ring oxygen atom. Analysis of the solvolysis product ratios indicates that the 2-deoxyglucosyl oxacarbenium ion is not solvent-equilibrated in the solvent mixtures studied. In the solvolysis of compound 1, the solvent trifluoroethanol facilitates diffusional separation of the leaving group and, in so doing, promotes the formation of the retained trifluoroethyl glycoside

  在含水甲醇，乙醇，三氟乙醇以及乙醇和三氟乙醇的二元混合物中监测2-脱氧-α-和β-D-吡喃葡萄糖基4'-溴代异喹啉鎓四氟硼酸盐的溶剂化物（1和2）。观察到的速率常数与通过解离（D（N）A（N））过渡态进行的1和2的溶剂解一致。与α-异头物相比，β-化合物的溶剂分解使过渡态电荷离域到环氧原子上更大。溶剂分解产物比率的分析表明，在所研究的溶剂混合物中，2-脱氧葡萄糖基氧杂碳鎓离子未达到溶剂平衡。在化合物1的溶剂分解中，溶剂三氟乙醇有助于离去基团的扩散分离，因此，