1,2,3-tri-O-acetyl-β-D-glucopyranose | 27539-66-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,3-tri-O-acetyl-β-D-glucopyranose
• 英文别名: [(2S,3R,4S,5R,6R)-2,3-diacetyloxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl] acetate
• CAS: 27539-66-8
• 化学式: C₁₂H₁₈O₉
• 分子量: 306.27
• InChiKey: GNYSCNOUXJBUSG-RMPHRYRLSA-N

物化性质

• 沸点：
  421.4±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,2,3-tri-O-acetyl-β-D-glucopyranose 在 吡啶 、 N-碘代丁二酰亚胺 、 palladium 10% on activated carbon 、 三氟化硼乙醚 、 氢气 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 111.67h， 生成 (2-adamantyl) 3-O-acetyl-2-O-tert-butyldimethylsilyl-β-D-idopyranoside
  参考文献：
  名称：

  亚苄基保护的 β-d-吡喃碘苷的 C7 差向异构化为 Idose 构象灵活性带来了结构见解

  摘要：

  Idose 在其他己醛糖中是独一无二的，因为它在溶液中具有高度的构象灵活性。我们在此表明​​亚苄基乙缩醛保护的 3- O-酰基-β- d-吡喃吡喃苷经历了路易斯酸催化的 C7 差向异构化，并伴随有4 C 1至1 C 4环反转。通过广泛的糖基化研究结合 NMR 分析、X 射线衍射和量子分子建模，已经彻底研究了发生这种转变的反应条件和结构参数。除了报告直接的 β-立体选择性 idosylation 方法外，我们的工作还为 idose 的构象灵活性带来了基本的结构见解。

  DOI：

  10.1021/acs.joc.2c01504
• 作为产物：
  描述：

  β-D-葡萄糖五乙酸酯 在 氯化锑(V) 、 sodium acetate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以38%的产率得到1,2,3-tri-O-acetyl-β-D-glucopyranose
  参考文献：
  名称：

  亚苄基保护的 β-d-吡喃碘苷的 C7 差向异构化为 Idose 构象灵活性带来了结构见解

  摘要：

  Idose 在其他己醛糖中是独一无二的，因为它在溶液中具有高度的构象灵活性。我们在此表明​​亚苄基乙缩醛保护的 3- O-酰基-β- d-吡喃吡喃苷经历了路易斯酸催化的 C7 差向异构化，并伴随有4 C 1至1 C 4环反转。通过广泛的糖基化研究结合 NMR 分析、X 射线衍射和量子分子建模，已经彻底研究了发生这种转变的反应条件和结构参数。除了报告直接的 β-立体选择性 idosylation 方法外，我们的工作还为 idose 的构象灵活性带来了基本的结构见解。

  DOI：

  10.1021/acs.joc.2c01504

文献信息

• A New Approach to Some 1,6-Dideoxy 1,6-Epithio Sugars
  作者：H Driguez、JC Mcauliffe、RV Stick、DMG Tilbrook、SJ Williams

  DOI：10.1071/ch9960343

  日期：——

  The treatment of hexopyranosyl bromides, also activated at C6 (Br, OTs, OMs), with H2S/HCONMe2 under basic conditions gives rise to 1,6-dideoxy 1,6-epithio sugars. One such sugar has been further transformed into the synthetically useful 3,4-anhydro-1,6-dideoxy-1,6-epithio-β-D-galactose. The treatment of this epoxide with sodium azide and with cyclohexylamine is described. An analogous treatment of one doubly activated hexopyranosyl bromide with sodium hydrogen selenide has led to a novel 1,6-dideoxy 1,6-episeleno sugar which displayed interesting n.m.r. spectra. Finally, in an attempt to prepare 1,6-dideoxy 1,6-epidithio sugars, a tetraalkylammonium tetrathiomolybdate reagent was found to be the reagent of choice for converting doubly activated hexopyranosyl bromides into 1,6-dideoxy 1,6-epithio sugars.

  在碱性条件下，用 H2S/HCONMe2 处理同样在 C6 处活化的溴化六吡喃糖（Br、OTs、OMs），会产生 1,6-二脱氧 1,6-epithio 糖。其中一种糖被进一步转化为对合成有用的 3,4-脱氢-1,6-二脱氧-1,6-环硫代-β-D-半乳糖。文中介绍了用叠氮化钠和环己胺处理这种环氧化物的方法。用硒化氢钠对一种双活化的溴化六吡喃糖进行类似处理后，得到了一种新型的 1,6-二脱氧 1,6-episeleno 糖，它显示出有趣的 n.m.r. 光谱。最后，在尝试制备 1,6-二脱氧 1,6-epidithio 糖时，发现四烷基钼酸四铵试剂是将双活化溴化己吡喃糖基转化为 1,6-二脱氧 1,6-epithio 糖的首选试剂。
• Synthesis of glycyrrhetic acid diglycosides and their cytoprotective activities against CCl4--induced hepatic injury in vitro
  作者：S Saito、S Nagase、M Kawase、Y Nagamura

  DOI：10.1016/0223-5234(96)89552-3

  日期：1996.1

  Glycyrrhetic acid diglycosides 16, 24, 25, 42 and 46, with respectively beta-D-glucuronopyranosyl-(1-->3)-beta-D-glucopyranose, -(1-->6)-alpha-D-glucopyranose, -(1-->6)-beta-D-glucopyranose, -(1-->6)-beta-D-galactopyranose, and beta-D-galacturonopyranosyl-(-->2)-beta-D-glucopyranose as sugar components at the O-3 positions on the aglycons, were synthesized. In vitro cytoprotective activities, against CCl4-induced hepatic injury, of the synthetic diglycosides, methyl beta-D-glucuronopyranosyl-(1-->4)-alpha-D-glucopyranosyl-D-glycyrrhetinate 33 and methyl esters 15 and 23 (the precursors of 16 and 24 respectively) were compared with those of glycyrrhizin 1 and beta-D-glucuronopyranosyl-(1-->2)-beta-D-glucopyranosyl-glycyrrhetic acid 2. Of the glycosides 16, 24, and 25, with beta-D-glucuronopyranosyl-glucopyranose as the sugar component, 16 and 24 were as cytoprotective as 1 and 2, whereas 25 showed no remarkable activity. From stereomodels of the glycosides these differences in activity were inferred to be due to the stereochemistries of the terminal beta-D-glucuronopyranoses in the molecules. Glycoside 46, in which the terminal beta-D-glucuronopyranose of 2 was replaced by beta-D-galacturonopyranose, was as potent as 2. Further, it was confirmed that a free COOH group on the E ring of aglycon was essential for the activity.
• Synthesis of O-methylsulfonyl derivatives of d-glucose as potential alkylating agents for targeted drug delivery to the brain. Evaluation of their interaction with the human erythrocyte GLUT1 hexose transporter
  作者：Thérèse Halmos、Monique Santarromana、Kostas Antonakis、Daniel Scherman

  DOI：10.1016/s0008-6215(96)00328-x

  日期：1997.3

  In order to obtain hydrophilic analogues of 1,4-dimethylsulfonyloxybutane (busulfan) with enhanced selectivity and improved brain penetration, we have synthesized 6-O-methylsulfonyl-D-glucose, 3-O-methylsulfonyl-D-glucose, 3,6-di-O-methylsulfonyl-D-glucose, 4-O-methylsulfonyl-D-glucose, and 4,6-di-O-methylsulfonyl-D-glucose, and we have studied their interactions with the human erythrocyte GLUT1 hexose transport system. Mesylation of OH-4 and OH-6 of glucose resulted in a slightly diminished affinity for the GLUT1 glucose transporter, whereas mesylation of OH-3 led to complete loss of affinity. (C) 1997 Elsevier Science Ltd.
• KANIE, OSAMU;TAKEDA, TADAHIRO;OGIHARA, YUKIO, J. CARBOHYDR. CHEM., 9,(1990) N-3, C. 159-165
  作者：KANIE, OSAMU、TAKEDA, TADAHIRO、OGIHARA, YUKIO

  DOI：——

  日期：——