but-2-yne-1,4-diyl bis(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside) | 428865-11-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: but-2-yne-1,4-diyl bis(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside)
• 英文别名: [(2R,3S,6S)-3-acetyloxy-6-[4-[[(2R,3S,6S)-3-acetyloxy-2-(acetyloxymethyl)-3,6-dihydro-2H-pyran-6-yl]oxy]but-2-ynoxy]-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 428865-11-6
• 化学式: C₂₄H₃₀O₁₂
• 分子量: 510.495
• InChiKey: SQXMAPQMMNRCET-PQZIIDKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  but-2-yne-1,4-diyl bis(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside) 、 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 以 甲苯 为溶剂， 以71%的产率得到1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-5-yl)-4-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranos-1-yloxymethyl)-5-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranos-1-yloxymethyl)-1,2,3-1H-triazole
  参考文献：
  名称：

  Application of click chemistry towards an efficient synthesis of 1,2,3-1H-triazolyl glycohybrids as enzyme inhibitors

  摘要：

  An efficient synthesis of novel 1,2,3-1H-triazolyl glycohybrids with two or more than two sugar units or a chromenone moiety via copper-catalysed azide-alkyne cycloaddition (CuAAC), a 1,3-dipolar cycloaddition of glycosyl azides to 2,3-unsaturated alkynyl glycosides or propargyloxy coumarins is described. The synthesised glycohybrids were screened for their a-glucosidase, glycogen phosphorylase and glucose-6-phosphatase inhibitory activities. A few of the glycohybrids showed promising inhibitory activities against these enzymes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.10.017
• 作为产物：
  描述：

  D-葡萄糖 在 copper(ll) sulfate pentahydrate 、 氢溴酸 、 sodium acetate 、 四氯化碲 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.67h， 生成 but-2-yne-1,4-diyl bis(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside) 、 but-2-yne-1,4-diyl bis(4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside)
  参考文献：
  名称：

  Stereoselective synthesis of pseudoglycosides catalyzed by TeCl4 under mild conditions

  摘要：

  Catalytic amounts of tellurium(IV) tetrachloride were used to promote the O-glycosylation of 3,4,6-tri-O-acetyl-D-glucal to give the corresponding 2,3-unsaturated-O-glycosides. With simple alcohols, the desired compounds were obtained in good yields and excellent anomeric selectivity in a short reaction time using only 2 mol % of the catalyst. The application of the method in the synthesis of a small set of glycopyranosides with rigid or flexible linkers gave the corresponding a anomers as products in good yields. Further applications of some of the synthesized compounds in allylation reaction of aldehydes gave the corresponding homoallylic alcohols in good yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.073

文献信息

• Aluminium triflate catalysed O-glycosidation: temperature-switched selective Ferrier rearrangement or direct addition with alcohols
  作者：D. Bradley G. Williams、Sandile B. Simelane、Henok H. Kinfe

  DOI：10.1039/c2ob25540e

  日期：——

  A temperature-controlled mechanism switch between the Al(OTf)3-catalysed direct addition of alcohols or the Ferrier rearrangement reactions in some glycals is presented. The scope and limitations are investigated as are the influence of the stereochemistry and nature of the protecting groups on the glycal substrate.

  提出了在Al（OTf）3催化的醇直接添加或某些糖基中的Ferrier重排反应之间的温度控制机制切换。研究了范围和局限性以及糖基上保护基的立体化学和性质的影响。
• An Expeditious Assembly of 3,4-Benzannulated 8-Oxabicyclo[3.2.1]octane Systems by [2+2+2] Alkyne Cyclotrimerisation: Total Synthesis of (–)-Bruguierol A
  作者：Chepuri V. Ramana、Sumanth R. Salian、Rajesh G. Gonnade

  DOI：10.1002/ejoc.200700648

  日期：2007.11

  Facile construction of benzene-fused 8-oxabicyclo[3.2.1]octane systems by employing a cross alkyne cyclotrimerisation reaction was explored. With this procedure, (–)-bruguierol A was synthesised, and its absolute configuration was established. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  探索了通过使用交叉炔环三聚反应轻松构建苯稠合的 8-氧杂双环 [3.2.1] 辛烷系统。通过此程序，合成了 (-)-bruguierol A，并确定了其绝对构型。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)