hexa-2,4-diyne-1,6-diyl bis(4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside) | 1400767-45-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: hexa-2,4-diyne-1,6-diyl bis(4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside)
• CAS: 1400767-45-4
• 化学式: C₂₆H₃₀O₁₂
• 分子量: 534.517
• InChiKey: QAXGDOHHAFNUGU-KTKTTYTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  38.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  142.12
• 氢给体数：
  0.0
• 氢受体数：
  12.0

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 1.67h， 生成 hexa-2,4-diyne-1,6-diyl bis(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside) 、 hexa-2,4-diyne-1,6-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