2-(2-(2-methoxyethoxy)ethoxy)ethanyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside | 1400767-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-(2-(2-methoxyethoxy)ethoxy)ethanyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• 英文别名: [(2R,3S,6S)-3-acetyloxy-6-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1400767-53-4
• 化学式: C₁₇H₂₈O₉
• 分子量: 376.404
• InChiKey: ALTKJJDHRZNNGU-BBWFWOEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(2-(2-methoxyethoxy)ethoxy)ethanyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 manganese(IV) oxide 、 水 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.58h， 生成 2-(2-(2-methoxyethoxy)ethoxy)ethanyl 2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose
  参考文献：
  名称：

  Structure-based design, synthesis and antitumoral evaluation of enulosides

  摘要：

  Enulosides, carbohydrate derivatives containing an alpha,beta-unsaturated carbonyl unit, were designed and obtained in high yields and isomeric purity. All synthesized compounds exhibited antitumoral activity in micromolar range against four tested tumor cells lines, being the best results observed for HL-60 cells. These compounds open new possibilities to prepare an array of more active, site-specific or selective antitumor agents. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.01.036
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 在 copper(ll) sulfate pentahydrate 、 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 1.75h， 生成 2-(2-(2-methoxyethoxy)ethoxy)ethanyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 、 2-(2-(2-methoxyethoxy)ethoxy)ethanyl 4,6-di-O-acetyl-2,3-dideoxy-β-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
• 作为试剂：
  描述：

  对硝基苯甲醛 、 烯丙基三氟硼酸钾 在 2-(2-(2-methoxyethoxy)ethoxy)ethanyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以93%的产率得到1-(4-硝基苯基)丁-3-烯-1-醇
  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 alpha 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.2012.07.070