<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>methyl tetra-O-acetyl-β-D-glucopyranoside | 34382-09-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>methyl tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: 1,2-O-isopropylidene-3-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-sn-glycerol；1,2-isopropylidene-3-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-sn-glycerol；(S)-2,2-dimethyl-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-ylmethyl)dioxolane；3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,2-O-isopropylidene-sn-glycerol；1,2-isopropylidene-3-O-(β-D-2,3,4,6-tetra-O-acetyl-glucopyranosyl)-(S)-glycerol
• CAS: 34382-09-7
• 化学式: C₂₀H₃₀O₁₂
• 分子量: 462.451
• InChiKey: JLGOOOITHPUWCR-SWAOIJHYSA-N

物化性质

• 沸点：
  508.1±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.24
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  142.12
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  <(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>methyl tetra-O-acetyl-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 生成 1,2-O-isopropylidene-3-O-(β-D-glucopyranosyl)-sn-glycerol
  参考文献：
  名称：

  A hydrophobic disordered peptide spontaneously anchors a covalently bound RNA hairpin to giant lipidic vesicles

  摘要：

  核酸通过与肽共轭形成脂质体的外源性分隔，为早期可进化的RNA-肽“协作”提供了实验支持。

  DOI：

  10.1039/c4ob00721b
• 作为产物：
  描述：

  2,3,4,5-tetra-O-acetyl-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 生成 <(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>methyl tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  基于二氢硬脂酸的单葡糖基二酰基甘油及其类似物的合成及其生物学评价

  摘要：

  在本研究中，使用三氯乙亚氨酸酯方法合成了β-构型的植物乳杆菌糖脂（GL1）分子及其脂肪酸类似物。使用2D-ROESY（NOE）和J耦合分析的NMR研究明确确定了GL1分子的β-构型。使用Furukawa试剂合成二氢硬脂酸，并在0°C下用EDC-HCl实现甘油在C-3位置的二氢硬脂酸的选择性酯化。评估了GL1分子及其脂肪酸类似物对DU145，A549，SKOV3和MCF7细胞系的体外细胞毒性。在所有合成的分子中，GL1分子和化合物7d表现出中等活性，而该化合物图7b显示了针对所有测试的细胞系的有希望的活性，其IC 50值分别为20.1、18.2、19.1和17.6μM。此外，所有测试的化合物对正常的HUVEC细胞均显示出较弱的细胞毒性。与未处理的细胞相比，当用化合物7b处理时，MCF7细胞显示出较低的溴脱氧尿苷掺入水平，表明化合物7b是高度有效的并且抑制了细胞增殖。此外，这些化合物通过诱导MCF

  DOI：

  10.1016/j.ejmech.2015.12.048

文献信息

• Glucose-Nucleobase Pseudo Base Pairs: Biomolecular Interactions within DNA
  作者：Empar Vengut-Climent、Irene Gómez-Pinto、Ricardo Lucas、Pablo Peñalver、Anna Aviñó、Célia Fonseca Guerra、F. Matthias Bickelhaupt、Ramón Eritja、Carlos González、Juan C. Morales

  DOI：10.1002/anie.201603510

  日期：2016.7.18

  Noncovalent forces rule the interactions between biomolecules. Inspired by a biomolecular interaction found in aminoglycoside–RNA recognition, glucose‐nucleobase pairs have been examined. Deoxyoligonucleotides with a 6‐deoxyglucose insertion are able to hybridize with their complementary strand, thus exhibiting a preference for purine nucleobases. Although the resulting double helices are less stable

  非共价力决定生物分子之间的相互作用。受氨基糖苷-RNA识别中发现的生物分子相互作用的启发，已检查了葡萄糖-核碱基对。插入有6个脱氧葡萄糖的脱氧寡核苷酸能够与其互补链杂交，因此表现出对嘌呤核苷碱基的偏好。尽管产生的双螺旋比自然螺旋的稳定性差，但它们仅表现出较小的局部变形。6-脱氧葡萄糖保持完全整合在双螺旋中，其OH基团与相对的鸟嘌呤形成两个氢键。这对6-脱氧葡萄糖-鸟嘌呤非常类似于嘌呤-嘧啶的几何形状。量子化学计算表明，葡萄糖-嘌呤对与天然T-A对一样稳定。
• The Synthesis of Optically Pure Epoxy-alkyl β-D-Glucosides and β-Cellobiosides as Active-Site Directed Inhibitors of Some β-Glucan Hydrolases
  作者：EB Rodriguez、GD Scally、RV Stick

  DOI：10.1071/ch9901391

  日期：——

  (2R)- and (2S)-2,3-Epoxypropyl, (3R)- and (3S)-3,4-epoxybutyl and (4S)- 4,s-epoxypentyl B- Dglucopyranoside , together with the (3R)- and (3s)-3,4-epoxybutyl β- cellobiosides , have been prepared by condensation of a glycosyl bromide with the appropriate enantiomer of a chiral alcohol containing a diol protected as an isopropylidene acetal, and subsequent manipulation of the unmasked diol into the epoxide function. As well, in an improvement to the whole process, both diastereoisomers of the various epoxypropyl and epoxybutyl glycosides were available from just the one enantiomer of the alcohol by an alternative manipulation of the diol. Finally, precursors to 2,3-epoxy-4-hydroxybutyl β-D-glucosides and β- cellobiosides were prepared in high optical purity by Sharpless asymmetric epoxidation of the appropriate 4-hydroxybut-2-enyl glycosides.

  (2R)-和(2S)-2,3-环氧丙基、(3R)-和(3S)-3,4-环氧丁基和(4S)-4,s-环氧戊基 B-吡喃葡萄糖苷，以及(3R)-和(3S)-3,4-环氧丁基 β-胞二糖苷、的制备方法是将溴化糖基与含有作为异亚丙基缩醛保护的二元醇的手性醇的适当对映体缩合，然后将未掩蔽的二元醇与环氧化物官能团结合。此外，对整个过程进行改进后，只需通过对二元醇进行另一种操作，就可以从醇的一种对映体中获得各种环氧丙基和环氧丁基苷的非对映异构体。最后，通过对适当的 4-羟基丁-2-烯基苷进行 Sharpless 不对称环氧化反应，制备出了高光学纯度的 2,3-环氧-4-羟基丁基 β-D 葡糖苷和 β-纤维二糖苷的前体。
• An Alternative Approach for the Synthesis of Sulfoquinovosyldiacylglycerol
  作者：Tobias Sitz、Hendrik Domey、Judith Fischer、Sascha Rohn

  DOI：10.3390/molecules26144275

  日期：——

  standards on the market. Consequently, an alternative synthetic route for the comprehensive preparation of sulfolipids was established. Here, the synthesis of a sulfolipid with two identical saturated fatty acids is described exemplarily. The method opens possibilities for the preparation of a diverse range of interesting derivatives with different saturated and unsaturated fatty acids.

  Sulfoquinovosyldiacylglycerol (SQDG) 是一种糖脂，广泛存在于光合活性生物体中。近年来由于其生物活性而备受关注。同样，对纯素和功能性食品的需求不断增加，导致人们对硫脂等微量营养素及其对人类健康的生理影响越来越感兴趣。为了研究这种影响，需要参考材料来开发新的分析方法并为生物活性的模型研究提供足够的材料。然而，这些材料的可用性受到从天然来源分离和纯化硫脂的困难以及市场上化学标准的不可用性的限制。因此，建立了一条综合制备硫脂的替代合成路线。这里，示例性地描述了具有两个相同饱和脂肪酸的硫脂的合成。该方法为用不同的饱和和不饱和脂肪酸制备各种有趣的衍生物开辟了可能性。
• RCM-Based Synthesis of a Variety of β-<i>C</i>-Glycosides and Their in Vitro Anti-Solid Tumor Activity
  作者：Maarten H. D. Postema、Jared L. Piper、Russell L. Betts、Frederick A. Valeriote、Halina Pietraszkewicz

  DOI：10.1021/jo040254t

  日期：2005.2.1

  The synthesis of a number of biologically relevant C-glycosides has been carried out through the use of an esterification-ring-closing metathesis (RCM) strategy. The required acid precursors were readily prepared via a number of standard chemical transformations followed by dehydrative coupling of these acids with several olefin alcohols 1 to yield the precursor esters 3 in excellent yield. Methylenation of the esters 3 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected beta-C-glycosides 6 in good overall yield. Several examples were converted to the corresponding C-glycoglycerolipids 17 and subsequently screened against solid-tumor cell lines for in vitro differential cytotoxicity.
• Synthesis and mesogenic properties of glycosyl diacylglycerols
  作者：H.M von Minden、M Morr、G Milkereit、E Heinz、V Vill

  DOI：10.1016/s0009-3084(01)00202-x

  日期：2002.1

  We synthesised glycosyl diacylglycerols bearing unsaturated or chiral methyl branched fatty acid chains. The thermotropism was measured with polarising microscopy and additionally the lyotropism with the contact preparation method. The synthesised compounds displayed thermotropic S-A (lamellar), cubic and columnar phases and investigation of the lyotropic phase behaviour led to the observation of inverted bicontinuous cubic V-H phases, lamellar L-x phases and normal bicontinuous cubic V-I phases, The phases are discussed with respect to the chemical structures that have been varied systematically to derive structure-property relationships. (C) 2002 Elsevier Science Ireland Ltd. All rights reserved.