Allyl 2,3,4-Tri-O-acetyl-β-D-xylopyranoside | 39102-79-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Allyl 2,3,4-Tri-O-acetyl-β-D-xylopyranoside
• 英文别名: Acetic acid 4,5-diacetoxy-2-allyloxy-tetrahydro-pyran-3-YL ester；[(3R,4S,5R,6R)-4,5-diacetyloxy-6-prop-2-enoxyoxan-3-yl] acetate
• CAS: 39102-79-9
• 化学式: C₁₄H₂₀O₈
• 分子量: 316.308
• InChiKey: FZUCCEUXHRAFLK-XJFOESAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Allyl 2,3,4-Tri-O-acetyl-β-D-xylopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以84%的产率得到allyl β-D-xylopyranoside
  参考文献：
  名称：

  Regioselective protection strategies for D-xylopyranosides

  摘要：

  The acylation of D-xylopyranosides can be effected at any position by selective hydroxyl activation with dibutyltin oxide in refluxing benzene and proper choice of starting anomer. Methyl 4-O-benzyl-beta-D-xylopyranoside, available from methyl 2,3-O-isopropylidene-beta-D-xylopyranoside, provides the 2- and 3-benzoates, which are easily separable in 85% combined yield. Methyl and allyl beta-D-xylopyranosides, when treated with 1 equiv of dibutyltin and subsequently with benzoyl chloride (1 equiv), yield their corresponding 4-benzoates (80%). The use of 2 equiv of benzoyl chloride provides the 3,4-dibenzoates in excellent yield (90%). The clean conversion to mono- or dibenzoates, depending on the amount of benzoyl chloride added, suggests that the intermediate stannylene acetals provide different activation levels. A pathway involving acylation of an intermediate dibutylchlorostannyl ether is proposed to explain the observed phenomenon. This sequential selective activation is used to afford protection and differentiation of the 3- and 4-positions with a one-pot synthesis of methyl 4-O-benzoyl-3-O-(chloroacetyl)-beta-D-xylopyranoside. Methyl and benzyl alpha-D-xylopyranosides afford the 2,4-dibenzoates in good yield (> 80%) demonstrating 1,3-activation of a triol system. This protection strategy is used to prepare benzyl O-(2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl)-(1 --> 3)-2,4-di-O-benzoyl-alpha-D-xylopyranoside from D-xylose and L-arabinose. In the final step, the silver triflate catalyzed glycosylation of benzyl 2,4-di-O-benzoyl-alpha-D-xylopyranoside by 2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl chloride is accomplished in 91% yield.

  DOI：

  10.1021/jo00025a013
• 作为产物：
  描述：

  D-吡喃木糖 在 吡啶 、 sodium hydride 作用下， 以 various solvent(s) 为溶剂， 反应 12.0h， 生成 Allyl 2,3,4-Tri-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  Klotz, Wolfgang; Schmidt, Richard R., Liebigs Annalen der Chemie, 1993, # 6, p. 683 - 690

  摘要：

  DOI：

文献信息

• Synthesis and biological activities of inositol 1,4,5-trisphosphate mimics related to xylopyranosides
  作者：N. Moitessier、F. Chrétien、Y. Chaplcur、C. Humeau

  DOI：10.1016/0040-4039(95)01677-a

  日期：1995.10

  2', 3, 4-trisphosphates of (2-hydroxyethyl) alpha- and beta-D-xylopyranosides and 3', 3, 4-trisphosphates of (3-hydroxypropyl) alpha- and beta-D-xylopyranosides have been prepared from allyl-D-xylosides and showed agonistic properties toward inositol 1, 4, 5-trisphosphate receptor.