C-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-methanol | 13121-49-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: C-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-methanol
• 英文别名: 1,5-anhydro-2,3,4-tri-O-benzyl-D-glucitol；2,3,4-tri-O-benzyl-1,5-anhydro-D-glucitol；[(2R,3R,4R,5S)-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanol
• CAS: 13121-49-8
• 化学式: C₂₇H₃₀O₅
• 分子量: 434.532
• InChiKey: OKRKDAAIOOFVSA-HVWQDESWSA-N

物化性质

• 熔点：
  79 °C
• 沸点：
  575.3±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  C-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-methanol 在 正丁基锂 、 草酰氯 、 三氟化硼乙醚 、 sodium methylate 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 22.17h， 生成
  参考文献：
  名称：

  Synthesis of aromatic C-xylosides by position inversion of glucose

  摘要：

  Two formally C-xylosylated analogs to 2-naphthyl beta-D-xylopyranoside, which is known to initiate priming of glucosaminoglycan chains, were synthesized by a position inversion of glucose (i.e., position I becomes position 5). The D-C-xyloside showed priming, while the L-C-xyloside did not initiate priming. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.068
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 palladium on activated charcoal 吡啶 、 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 、 氢气 、 potassium hydride 、 sodium hydride 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 66.0h， 生成 C-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-methanol
  参考文献：
  名称：

  A New Strategy for the Stereoselecitve Syntheses of C-Glycosyl Compounds of β-Pentapyranoses

  摘要：

  The C-glycosyl compounds of beta-L-xylopyranose and beta-D-arabinopyranose were conveniently prepared by reduction of methyl alpha-D-glucopyranoside and methyl alpha-D-mannopyranoside with triethylsilane in the presence of trimethylsilyl trifluoromethanesulfonate, respectively.

  DOI：

  10.1080/00397919608003565

文献信息

• Synthesis and Comparative Structure–Activity Study of Carbohydrate-Based Phenolic Compounds as α-Glucosidase Inhibitors and Antioxidants
  作者：Shota Machida、Saki Mukai、Rina Kono、Megumi Funato、Hiroaki Saito、Taketo Uchiyama

  DOI：10.3390/molecules24234340

  日期：——

  Twenty-one natural and unnatural phenolic compounds containing a carbohydrate moiety were synthesized and their structure–activity relationship (SAR) was evaluated for α-glucosidase inhibition and antioxidative activity. Varying the position of the galloyl unit on the 1,5-anhydro-d-glucitol (1,5-AG) core resulted in changes in the α-glucosidase inhibitory activity and notably, particularly strong activity was demonstrated when the galloyl unit was present at the C-2 position. Furthermore, increasing the number of the galloyl units significantly affected the α-glucosidase inhibition, and 2,3,4,6-tetra-galloyl-1,5-AG (54) and 2,3,4,6-tetra-galloyl-d-glucopyranose (61) exhibited excellent activities, which were more than 13-fold higher than the α-glucosidase inhibitory activity of acertannin (37). Moreover, a comparative structure-activity study suggested that a hemiacetal hydroxyl functionality in the carbohydrate core and a biaryl bond of the 4,6-O-hexahydroxydiphenoyl (HHDP) group, which are components of ellagitannins including tellimagrandin I, are not necessary for the α-glucosidase inhibitory activity. Lastly, the antioxidant activity increased proportionally with the number of galloyl units.

  合成了二十一种含有碳水化合物基团的天然和非天然酚类化合物，并评估了它们在α-葡萄糖苷酶抑制和抗氧化活性方面的结构-活性关系（SAR）。在1,5-脱氧-D-葡萄糖醇（1,5-AG）核心上改变没食子酸单元的位置导致了α-葡萄糖苷酶抑制活性的变化，特别是当没食子酸单元位于C-2位置时表现出明显的强活性。此外，增加没食子酸单元的数量显著影响了α-葡萄糖苷酶抑制作用，2,3,4,6-四没食子酸-1,5-AG（54）和2,3,4,6-四没食子酸-D-葡萄糖吡喃糖（61）表现出卓越的活性，其α-葡萄糖苷酶抑制活性比没食子酸（37）高出13倍以上。此外，一项比较结构-活性研究表明，碳水化合物核心中的半缩醛羟基官能团和4,6-O-六羟基二苯甲酰（HHDP）单元的双芳基键，包括tellimagrandin I在内的椰子酸鞣质并不是α-葡萄糖苷酶抑制活性所必需的。最后，抗氧化活性随没食子酸单元数量的增加而成比例增加。
• Triisobutylaluminium and Diisobutylaluminium Hydride as Molecular Scalpels: The Regioselective Stripping of Perbenzylated Sugars and Cyclodextrins
  作者：Thomas Lecourt、Alexandre Herault、Alan J. Pearce、Matthieu Sollogoub、Pierre Sinaÿ

  DOI：10.1002/chem.200305683

  日期：2004.6.21

  mechanistic rationale critically involving the kinetic formation of a product-generating 2:1 Al-benzylated sugar complex. For the reaction to occur, one pair of adjacent oxygen atoms should first be able to form a chelation complex with the first equivalent of aluminium reagent, either a highly fluxional complex with tetracoordinate aluminium species or a pentacoordinate one. The second equivalent then

  为了解释氢化二异丁基铝（DIBAL-H）和三异丁基铝（TIBAL）对聚苄基糖或环糊精具有显着的区域选择性脱O-苄基化性能，我们提出了一种合理的机理原理，主要涉及动力学生成产物2：1 Al的动力学形成-苄基糖复合物。为使反应发生，一对相邻的氧原子应首先能够与第一当量的铝试剂形成螯合络合物，该络合物可以是具有四配位铝物种的高通量配位化合物，也可以是五配位铝原子的高通量配位化合物。然后，第二个等价物通过优先与所选对中的一个氧原子配位，诱导脱-O-烷基化的区域选择性。
• C,O-SPIRO ARYL GLYCOSIDE COMPOUNDS, PREPARATION THEREFOR AND USE THEREOF
  申请人：Shanghai Institute of Materia Medica, Chinese Academy of Sciences

  公开号：EP3315502A1

  公开（公告）日：2018-05-02

  The present invention provides C, O-spiro aryl glycoside compounds, preparation therefor and use thereof. Specifically provided are the compounds represented by the formula (I), wherein the definitions of each group are described in the specification. The compound can be used as SGLT2 inhibitors in preparing the pharmaceutical compositions for treating diseases such as diabetes, atherosclerosis, adiposity and etc.

  本发明提供了 C、O-螺芳基苷化合物、其制备方法及其用途。具体提供了由式（I）表示的化合物，其中各组的定义在说明书中描述。该化合物可作为 SGLT2 抑制剂用于制备治疗糖尿病、动脉粥样硬化、脂肪肝等疾病的药物组合物。
• The temporary silicon connection method in the control of regio- and stereochemistry. Applications to radical-mediated reactions. The stereospecific synthesis of C-glycosides
  作者：Gilbert Stork、Hong Suk Suh、Guncheol Kim

  DOI：10.1021/ja00018a063

  日期：1991.8
• Ginnalin B induces differentiation markers and modulates the proliferation/differentiation balance via the upregulation of NOTCH1 in human epidermal keratinocytes
  作者：Atsushi Kato、Junna Koyama、Kenta Shinzawa、Shuki Imaeda、Isao Adachi、Robert J. Nash、George W.J. Fleet、Megumi Shintani、Chihiro Takeuchi、Fumihiro Ishikawa

  DOI：10.1016/j.bmc.2019.04.008

  日期：2019.6

  The red maple and sugar maple (Acer rubrum and A. saccharum, respectively) contain acertannins (ginnalins and maplexins), galloylated derivatives of 1,5-anhydro-D-glucitol (1,5-AG, 1). These compounds have a variety of potential medicinal properties and we have shown that some of them promote the expression of ceramide synthase 3. We now report on the beneficial effects of ginnalin B, (6-O-galloyl-1,5-AG, 5), leading to acceleration of skin metabolism and reduction of the turnover time. Ginnalin B dose-dependently increased the relative amount of keratin 10, keratin 1, and filaggrin gene, with maximal increase of 1.7-, 2.9, and 5.2-fold at 100 mu M, respectively. The validation study showed that it had superior capacity to induce multiple stages of keratinocyte differentiation and significantly elevated the immunostaining site of keratin 10 and filaggrin in a 3-dimensional cultured human skin model, by 1.2 and 2.8-fold, respectively. Furthermore, ginnalin B caused the arrest of proliferation at the G(0)/G(1) phase but it did not induce apoptotic cell death in normal human keratinocytes. Molecular studies revealed that ginnalin B up-regulated the levels of NOTCH1 and a concomitant increase p21 expression. Ginnalin B, therefore, represents a new class of promising functional and medical cosmetic compound and it could contribute to the maintenance of homeostasis of the epidermis.