benzyl 2-O-benzoyl-α-D-xylopyranoside | 18403-20-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-O-benzoyl-α-D-xylopyranoside
• 英文别名: [(2S,3R,4S,5R)-4,5-dihydroxy-2-phenylmethoxyoxan-3-yl] benzoate
• CAS: 18403-20-8
• 化学式: C₁₉H₂₀O₆
• 分子量: 344.364
• InChiKey: KVAZEKDRMGDVCF-NTDBWNAOSA-N

物化性质

• 沸点：
  521.3±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 2-O-benzoyl-α-D-xylopyranoside 在 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 碘仿 、 偶氮二异丁腈 、 cyanoborane 、 三丁基氯化锡 、 水 、 三乙胺 、 三苯基膦 作用下， 以 吡啶 、 甲醇 、 水 、 二甲基亚砜 、 甲苯 、 叔丁醇 为溶剂， 反应 85.0h， 生成 benzyl 4-<2-(phenylsulfonyl)ethyl>-4-deoxy-β-L-lyxopyranoside
  参考文献：
  名称：

  An approach to pseudomonic acids from D-xylose

  摘要：

  DOI：

  10.1021/jo00242a017
• 作为产物：
  描述：

  D-吡喃木糖 在 二正丁基氧化锡 、 乙酰氯 作用下， 反应 24.0h， 生成 benzyl 2-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

• Regiospecific ring-opening reactions of benzyl 3,4-anhydro-.alpha.-D-ribopyranoside with nucleophiles: a systematic study
  作者：M. Vaman Rao、M. Nagarajan

  DOI：10.1021/jo00241a012

  日期：1988.3
• VAMAN, RAO M.;NAGARAJAN, M., J. ORG. CHEM., 53,(1988) N 7, 1432-1437
  作者：VAMAN, RAO M.、NAGARAJAN, M.

  DOI：——

  日期：——