2-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]acetic acid | 557087-95-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]acetic acid
• CAS: 557087-95-3
• 化学式: C₃₆H₃₈O₇
• 分子量: 582.694
• InChiKey: VFYNVTKGNSXJFR-UGOGRBCTSA-N

物化性质

• 熔点：
  102.5-103.8 °C
• 沸点：
  722.8±60.0 °C(predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]acetic acid 在 三甲基乙酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 4'-chloro-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)acetophenone
  参考文献：
  名称：

  β-葡萄糖gallin C-类似物的合成和醛糖还原酶抑制研究

  摘要：

  β-糖蛋白1（BGG）是从印度醋栗（Emblica officinalis）药用植物中分离出的主要成分，是有效的，选择性的醛糖还原酶（AKR1B1）抑制剂。尚未开发出其中-CH 2-单元取代葡糖基-O的C-类似物的合成方法。尤其是C-类似物4的合成及其醛糖还原酶抑制（ARI）活性的研究。

  DOI：

  10.1002/ejoc.201701468
• 作为产物：
  描述：

  (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanal 在 sodium chlorite 、 potassium dihydrogenphosphate 、 双氧水 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以100%的产率得到2-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]acetic acid
  参考文献：
  名称：

  碳链糖基氨基酸新家族的Hantzsch型三组分方法。C-糖基甲基吡啶基丙氨酸的合成† ，‡

  摘要：

  本文报道的C-糖基甲基吡啶基丙氨酸构成了一个新的糖基氨基酸家族，其中包含连接碳水化合物和氨基酸残基的吡啶环。这些氨基酸可用于制备通过刚性和高度稳定的系链显示牢固结合的碳水化合物片段的非天然糖肽。通过使用醛-酮酸酯-烯胺酯系统的热诱导汉茨型环缩合，已经开辟了通往这些新杂合分子的可行途径。在这些试剂之一上连接一个C-糖基残基，而另一个残基结合了一个氨基酸片段。在单锅法优化方法中，未分离出二氢吡啶，而使用聚合物负载的清除剂通过去除未反应的物质和副产物进行纯化。然后用聚合物结合的氧化剂将二氢吡啶（非对映异构体的混合物）氧化，得到带有两个生物活性残基的目标吡啶。通过这种方法，制备了八种化合物（收率58-68％），其中多样性的元素是（i）吡喃糖环的葡萄糖和半乳糖构型，（ii）异头异构体的α-和β-构型（iii）吡啶环中碳水化合物和氨基酸部分的位置。

  DOI：

  10.1021/jo071221r

文献信息

• Synthesis and Biological Evaluation of α- and β-6-Amido Derivatives of 17-Cyclopropylmethyl-3, 14β-dihydroxy-4, 5α-epoxymorphinan: Potential Alcohol-Cessation Agents
  作者：Senait Ghirmai、Marc R. Azar、Wilma E. Polgar、Ilona Berzetei-Gurske、John R. Cashman

  DOI：10.1021/jm701060e

  日期：2008.3.1

  and aliphatic amide analogues of 6-naltrexamine were synthesized and used to characterize the binding to and functional activity of human mu-, delta-, and kappa-opioid receptors. Competition binding assays showed 11-25 and 27-31 bound to the mu (K(i) = 0.05-1.2 nM) and kappa (K(i) = 0.06-2.4 nM) opioid receptors. Compounds 11-18 possessed significant binding affinity for the delta receptor (K(i) = 0

  合成了6-纳曲胺的取代的芳基和脂族酰胺类似物，并用于表征与人μ-，δ-和κ-阿片受体的结合和功能活性。竞争结合测定表明11-25和27-31与mu（K（i）= 0.05-1.2 nM）和kappa（K（i）= 0.06-2.4 nM）阿片受体结合。化合物11-18对δ受体具有显着的结合亲和力（K（i）＝ 0.8-12.4nM）。功能测定显示几种化合物充当δ或κ受体的部分或全部激动剂，同时在μ受体上保留拮抗剂特征。芳基酰胺的结构-活性关系表明，有效的化合物具有亲脂性基团或能够氢键键合的取代基。代谢稳定性研究表明，在存在大鼠的情况下，11、12和14具有相当大的稳定性，小鼠或人类肝脏制剂。使用手术技术对11大鼠进行10％乙醇自我给药抑制的ED 50为0.5 mg / kg。
• Synthesis and in vitro biological evaluation of a carbon glycoside analogue of morphine-6-glucuronide
  作者：James M. MacDougall、Xiao-Dong Zhang、Willma E. Polgar、Taline V. Khroyan、Lawrence Toll、John R. Cashman

  DOI：10.1016/j.bmcl.2005.01.072

  日期：2005.3

  Attachment of a glucose moiety to 6-beta-aminomorphine afforded compound 3, where the glucose moiety was linked to the C-6 nitrogen atom by a two-carbon bridge. The synthesis of 3 was accomplished in eight steps from 3-triisopropylsilyl-6-P-aminomorphine and 2,3,4,6-tetra-O-benzyl-D-glucose. The C-glycoside 3 was prepared with the objective of examining a metabolically stable analogue of morphine-6-glucuronide and determining the potency and selectivity of opioid receptor binding. Competition binding assays showed that 3 bound to the mu opioid receptor with a K-i value of 3.5 nM. The C-glycoside 3 exhibited delta/mu and kappa/mu selectivity ratios of 76 and 165, respectively. The synthetic intermediate (i.e., benzyl precursor, compound 11) bound to the mu opioid receptor with a K-i value of 0.5 nM, was less selective for the mu opioid receptor. The [S-35]GTP gamma S assay was used to evaluate the functional properties of compounds 3 and 11. Compound 3 was determined to be a full agonist at the p opioid receptor, whereas compound 11 was found to be a partial agonist. Compound 3 was determined to be very stable in the presence of human liver S9, and rat and monkey liver microsomes: no detectable loss of 3 was observed up to 90 min. Compound 3 was also very stable at pH 2 and pH 7.4, suggesting that 3 possessed properties for sustained duration of action. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and Partial Biological Evaluation of a Small Library of Differentially-Linked β-<i>C</i>-Disaccharides¹
  作者：Maarten H. D. Postema、Jared L. Piper、Lei Liu、Jie Shen、Marcus Faust、Peter Andreana

  DOI：10.1021/jo030039x

  日期：2003.6.1

  The synthesis of a small library of differentially-linked beta-C-disaccharides has been carried out through the use of a radical allylation-RCM strategy. Acids 6 were prepared by Keck allylation of a suitable carbohydrate-based radical precursor, followed by oxidative cleavage of the formed alkene. Dehydrative coupling of these acids with the known olefin alcohol 5 then gave the precursor esters 7 in excellent yield. Methylenation of the esters 7 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected beta-C-disaccharides 10 in good overall yield. Five examples were then deprotected and screened for their efficacy as enzyme inhibitors of beta-glycosidase and against several solid-tumor cell lines for in vitro differential cytotoxicity.