1,2-O-isopropylidene-3-O-(β-D-glucopyranosyl)-sn-glycerol | 76739-15-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-3-O-(β-D-glucopyranosyl)-sn-glycerol
• 英文别名: 1,2-isopropylidene-3-O-(β-D-glucopyranosyl)-(S)-glycerol
• CAS: 76739-15-6
• 化学式: C₁₂H₂₂O₈
• 分子量: 294.302
• InChiKey: RLCCJHDTKQGEDP-OVHRRVLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.05
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  117.84
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-3-O-(β-D-glucopyranosyl)-sn-glycerol 在 吡啶 、 palladium 10% on activated carbon 、 氢气 、 四丁基碘化铵 、 sodium hydride 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 20.0 ℃ 、506.66 kPa 条件下， 反应 17.0h， 生成 3-O-β-D-glucopyranosyl-1,2-di-O-hexadecanoyl-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：

  <(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

文献信息

• 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。
• Synthesis of α- and β-glycopyranosides via 1-0-alkylation
  作者：R.R. Schmidt、U. Moering、M. Reichrath

  DOI：10.1016/0040-4039(80)80236-x

  日期：1980.1

  1-0-Alkylation of partly protected glucopyranose 1 and galactopyranose 13 led to a convenient, short term synthesis of β-glycosides and β-disaccharides 4a–d and 14. Glucopyranose 2 with a bulky protective group at 0–6 yielded exclusively the α-anomer (isomaltoside derivative) 5.

  部分保护的吡喃葡萄糖1和半乳糖吡喃糖13的1-0烷基化导致β-糖苷和β-二糖4a-d和14的便捷，短期合成。在0-6带有较大保护基的葡糖醛糖2仅产生α。 -异头物（异麦芽糖苷衍生物）5。
• 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.
• Stereospecific synthesis of retinoic acid glucoconjugates, as pseudo-substrates of epidermal β-glucocerebrosidase
  作者：Daniel Redoulès、Jacques Perié

  DOI：10.1016/s0040-4039(99)00920-x

  日期：1999.6

  The synthesis of glucocerebrosides (precursors of skin lipids) analogues bearing the bioactive compound retinoic acid is described; the two diastereoisomeric gluco-conjugates glucose-glycerol-retinoic acid are pseudo-subtrates for the title enzyme. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.