2-bromoethyl-4,6-di-O-acetyl-2,3-dideoxy-β-D-erythrohex-2-enopyranoside | 121668-36-8

• 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-bromoethyl-4,6-di-O-acetyl-2,3-dideoxy-β-D-erythrohex-2-enopyranoside
• CAS: 121668-36-8
• 化学式: C₁₂H₁₇BrO₆
• 分子量: 337.167
• InChiKey: FCHBDQNVSYVCRP-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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-溴乙醇 、 乙酰化葡萄烯糖 在 磷酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 2-bromoethyl-4,6-di-O-acetyl-2,3-dideoxy-β-D-erythrohex-2-enopyranoside 、 2-bromoethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  A convenient synthesis of pseudoglycosides via a Ferrier-type rearrangement using metal-free H3PO4 catalyst

  摘要：

  A mild and efficient synthesis of pseudoglycals has been developed using a metal-free catalytic system. Phosphoric acid proved to be an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-D-glycal to 2,3-unsaturated O-glycosides. A wide range of alcohols including naturally bioactive compounds could be coupled with the glycal to give the desired products in good to excellent yields and with high levels of alpha-selectivity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.11.103

文献信息

• IBr-Catalyzed O-Glycosylation of D-Glucals: Facile Synthesis of 2,3-Unsaturated-O-glycosides
  作者：Uthaiwan Sirion、Rungnapha Saeeng、Onanong Siripru

  DOI：10.3987/com-15-13174

  日期：——

  Iodine monobromide (IBr) is explored as an alternative catalyst for the selective synthesis of 2,3-unsaturated glycosides from tri-O-acetyl-D-glucal 1 with several alcohols through Ferrier rearrangement. This reaction was shown to be a simple, efficient and cost-effective method, affords twenty examples of corresponding glycoside products in high yields with good alpha-selectivity.
• Convenient one-pot synthesis of triazolylethyl-2,3-unsaturated-O-glycoside derivatives
  作者：Wadchara Mangsang、Uthaiwan Sirion、Rungnapha Saeeng

  DOI：10.1016/j.tet.2015.09.026

  日期：2015.11

  An efficient and convenient synthesis of new derivatives of triazolylethy1-2,3-unsaturated-O-glycoside has been developed using sequential one-pot glycosylation-azidation-CuAAc reactions procedure. Various substituted alkynes have been employed for the click reaction to obtain a variety of O-glycosylethyl triazole adducts in good to excellent yields with good alpha-anomeric selectivity. (C) 2015 Elsevier Ltd. All rights reserved.