1,1-dimethylprop-2-yn-1-yl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside | 1400767-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 1,1-dimethylprop-2-yn-1-yl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside
• 英文别名: 2-methyl but-3-yn-2-yl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside；2-methylbut-3-yn-2-yl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside
• CAS: 1400767-36-3
• 化学式: C₁₅H₂₀O₆
• 分子量: 296.32
• InChiKey: DSUQKIUJRAKSQA-MJBXVCDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.19
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 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 1.58h， 生成 1,1-dimethylprop-2-yn-1-yl 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

文献信息

• Synthesis of 2,3-Unsaturated Alkynyl O-Glucosides from Tri-O-acetyl-d-glucal by Using Montmorillonite K-10/Iron(III) Chloride Hexahydrate with Subsequent Copper(I)-Catalyzed 1,3-Dipolar Cycloaddition
  作者：Ronaldo de Oliveira、Valentina Melo、Willyenne Dantas、Celso Camara

  DOI：10.1055/s-0034-1378829

  日期：——

  within short times and with high α-stereoselectivities. Subsequently, the glucosides were coupled with 2-azido-1,4-naphthoquinone to produce a new series of 1,2,3-1H-triazolyl O-glucoside derivatives through a click reaction. Two strategies were considered for the synthesis of 2,3-unsaturated O-glucosyl-1,2,3-triazoles. The first, involving reaction between tri-O-acetyl-d-glucal and triazole alcohols

  摘要 考虑了两种合成2，3-不饱和O-葡萄糖基-1,2,3-三唑的策略。三-之间的第一，涉及反应ö乙酰基d -glucal和三唑醇没有给出立体选择性。第二种策略是通过Ferrier重排从糖和炔醇中提供2,3-不饱和的O-糖苷。该方法在二氯甲烷中使用掺有六水合氯化铁（III）的蒙脱石K-10，可在短时间内以高至优异的产率和高α-立体选择性提供新的糖苷。随后，将糖苷与2-叠氮基-1,4-萘醌偶联以生成新的1,2,3-1 H-三唑基O系列-葡萄糖苷衍生物通过点击反应。 考虑了两种合成2，3-不饱和O-葡萄糖基-1,2,3-三唑的策略。三-之间的第一，涉及反应ö乙酰基d -glucal和三唑醇没有给出立体选择性。第二种策略是通过Ferrier重排从糖和炔醇中提供2,3-不饱和的O-糖苷。该方法在二氯甲烷中使用掺有六水合氯化铁（III）的蒙脱石K-10，可在短时间内以高至优异的产率和高α-立体选择性