ethyl 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate | 82614-10-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate
• 英文别名: ethyl 3,7-anhydro-2-deoxy-4,5,6,8-tetra-O-benzyl-D-glycero-D-gulo-octonate；ethyl (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)ethanoate；ethyl 2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)acetate；ILS-JS-1A-6；ethyl 2-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]acetate
• CAS: 82614-10-6
• 化学式: C₃₈H₄₂O₇
• 分子量: 610.747
• InChiKey: WDROQFMHMFJWRY-PTEWCOKHSA-N

物化性质

• 沸点：
  694.7±55.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  45
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanal
  参考文献：
  名称：

  通过B-烷基铃木偶联聚合合成稠合多环醚的一般策略：雪茄毒素ABCD环片段的合成

  摘要：

  已经开发了一种用于稠合多环醚的会聚偶联的新方法，该方法依赖于内酯衍生的烯醇三氟甲磺酸酯或磷酸盐的B-烷基铃木交叉偶联。该策略已成功应用于收敛性合成的瓜瓜毒素的ABCD环片段4，瓜瓜毒素是导致瓜瓜鱼中毒的致病性毒素。合成途径包括B和D环（分别为18和29c）通过B烷基Suzuki偶合的收敛结合，在D环中引入双键，然后还原性闭合四氢吡喃C环以提供BCD环系统51，最后进行闭环易位反应，以构建氧杂环丁烯A环。

  DOI：

  10.1016/s0040-4020(02)00045-5
• 作为产物：
  描述：

  2-deoxy-4,5,6,8-tetra-O-benzyl-α-D-gluco-3,7-pyranoso-3-octulosonate 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 以86%的产率得到ethyl 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate
  参考文献：
  名称：

  Synthesis and in vitro biological evaluation of a carbon glycoside analogue of morphine-6-glucuronide

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2005.01.072

文献信息

• Building a Macrocyclic Toolbox from<i>C</i>-Linked Carbohydrates Identifies Antiangiogenesis Agents from Zebrafish Assay
  作者：Srinivas Jogula、Bhanudas Dasari、Mahender Khatravath、Gayathri Chandrasekar、Satish Srinivas Kitambi、Prabhat Arya

  DOI：10.1002/ejoc.201300548

  日期：2013.8

  We report the synthesis of four different types of macrocyclic-derived glycohybrids from carbohydrates that have an amino acid moiety in the large-ring skeleton. These macrocyclic glycohybrids were ...

  我们报告了从碳水化合物合成四种不同类型的大环衍生糖杂化物，这些碳水化合物在大环骨架中具有氨基酸部分。这些大环糖杂化物是...
• A general strategy for the convergent synthesis of fused polycyclic ethers via B-alkyl Suzuki coupling: synthesis of the ABCD ring fragment of ciguatoxins
  作者：Makoto Sasaki、Makoto Ishikawa、Haruhiko Fuwa、Kazuo Tachibana

  DOI：10.1016/s0040-4020(02)00045-5

  日期：2002.3

  rings (18 and 29c, respectively) by the B-alkyl Suzuki coupling, introduction of a double bond into the D ring followed by reductive closure of the tetrahydropyran C ring to afford the BCD ring system 51, and, finally, ring-closing metathesis reaction to construct the oxepene A ring.

  已经开发了一种用于稠合多环醚的会聚偶联的新方法，该方法依赖于内酯衍生的烯醇三氟甲磺酸酯或磷酸盐的B-烷基铃木交叉偶联。该策略已成功应用于收敛性合成的瓜瓜毒素的ABCD环片段4，瓜瓜毒素是导致瓜瓜鱼中毒的致病性毒素。合成途径包括B和D环（分别为18和29c）通过B烷基Suzuki偶合的收敛结合，在D环中引入双键，然后还原性闭合四氢吡喃C环以提供BCD环系统51，最后进行闭环易位反应，以构建氧杂环丁烯A环。
• A Ramberg−Bäcklund Approach to the Synthesis ofC-Glycosides,C-Linked Disaccharides, andC-Glycosyl Amino Acids
  作者：Duncan E. Paterson、Frank K. Griffin、Marie-Lyne Alcaraz、Richard J. K. Taylor

  DOI：10.1002/1099-0690(200204)2002:7<1323::aid-ejoc1323>3.0.co;2-8

  日期：2002.4

  dioxides using the Meyers variant of the Ramberg−Backlund rearrangement, are described. These include a formal synthesis of a β-glycosidase inhibitor 12 and an efficient route to spirocyclic glucose derivatives 17 and 18. The synthesis of C-linked disaccharides 24, 31, and 38 and the C-glycosyl amino acid 49 using the Ramberg−Backlund rearrangement is also reported. (© Wiley-VCH Verlag GmbH, 69451 Weinheim

  描述了使用 Ramberg-Backlund 重排的 Meyers 变体衍生自 S-糖苷二氧化物的外糖的合成应用。其中包括 β-糖苷酶抑制剂 12 的正式合成和生成螺环葡萄糖衍生物 17 和 18 的有效途径。 使用 Ramberg-Backlund 合成 C-连接的二糖 24、31 和 38 和 C-糖基氨基酸 49重排也有报道。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
• Ramberg-Bäcklund Approaches to the Synthesis of C-Linked Disaccharides
  作者：Frank K. Griffin、Duncan E. Paterson、Richard J. K. Taylor

  DOI：10.1002/(sici)1521-3773(19991004)38:19<2939::aid-anie2939>3.0.co;2-s

  日期：1999.10.4

  Readily available S-glycoside dioxides were utilized in a Ramberg-Bäcklund rearrangement for the construction of C-linked disaccharides. This approach is ideally suited to analogue synthesis simply by variation of the alkylating agent, and is illustrated here by the synthesis of beta,beta-C-trehalose (see reaction scheme), a higher homologue of C-trehalose, and methyl C-gentiobioside. Bn=benzyl.

  在Ramberg-Bäcklund重排中利用了现成的S-糖苷二氧化物来构建C键联的二糖。这种方法非常适合简单地通过烷基化剂的变化进行类似物合成，并且在此处通过β，β-C-海藻糖的合成（请参见反应方案），C-海藻糖的较高同源物和甲基C-龙胆生物苷进行说明。 。Bn ＝苄基。
• The Wittig-Horner reaction on 2,3,4,6-tetra-O-benzyl-D-mannopyranose and 2,3,4,6-tetra -O-benzyl-D-glucopyranose
  作者：Pietro Allevi、Pierangela Ciuffreda、Diego Colombo、Diego Monti、Giovanna Speranza、Paolo Manitto

  DOI：10.1039/p19890001281

  日期：——

  The synthetic utility of the Wittig-Horner reaction in the synthesis of C-glycosides is illustrated by the preparation of the α-and β-glycosyl acetates of the 2,3,4,6-tetra-O-benzyl-D-mannopyranose and of the 2,3,4,6-tetra-O-benzylglucopyranose. A partial epimerization of the C-2 carbon of the starting protected carbohydrate is observed.

  通过制备2,3,4,6-四-O-苄基-D-甘露吡喃糖和2,3,4,6-四-O-苄基吡喃葡萄糖的组成。观察到起始的受保护的碳水化合物的C-2碳部分差向异构。