methyl 2,4-di-O-benzoyl-α-D-xylopyranoside | 83158-21-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,4-di-O-benzoyl-α-D-xylopyranoside
• 英文别名: [(3R,4S,5R,6S)-5-benzoyloxy-4-hydroxy-6-methoxyoxan-3-yl] benzoate
• CAS: 83158-21-8
• 化学式: C₂₀H₂₀O₇
• 分子量: 372.375
• InChiKey: ZSQISKHYKGFPAK-YZLZLFLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,4-di-O-benzoyl-α-D-xylopyranoside 在 4 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 2.0h， 生成 methyl 3-O-α-L-rhamnopyranosyl-α-D-xyloside
  参考文献：
  名称：

  Kamiya, Shintaro; Esaki, Sachiko; Ito-Tanaka, Reiko, Agricultural and Biological Chemistry, 1985, vol. 49, # 8, p. 2351 - 2358

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酰氯 、 甲基-Alpha-D-吡喃木糖 在 二正丁基氧化锡 作用下， 生成 methyl 2,4-di-O-benzoyl-α-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

文献信息

• Tsuda, Yoshisuke; Haque, Md. Ekramul; Yoshimoto, Kimihiro, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 5, p. 1612 - 1624
  作者：Tsuda, Yoshisuke、Haque, Md. Ekramul、Yoshimoto, Kimihiro

  DOI：——

  日期：——
• Selective benzoylation of methyl α- and β-d-xylopyranoside
  作者：Yôtaro Kondo

  DOI：10.1016/s0008-6215(00)80551-0

  日期：1982.9