para-tolyl 2-O-allyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside | 807333-76-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: para-tolyl 2-O-allyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside
• CAS: 807333-76-2
• 化学式: C₃₇H₄₀O₅S
• 分子量: 596.788
• InChiKey: ODWQDYVHIFGWTL-GDWCTEMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.77
• 重原子数：
  43.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  para-tolyl 2-O-allyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 在 Wilkinson's catalyst 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.17h， 生成 para-tolyl 3,4,6-tri-O-benzyl-2-O-(prop-1-enyl)-1-thio-α-D-mannopyranoside 、 para-tolyl 3,4,6-tri-O-benzyl-2-O-(prop-1-enyl)-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Allyl protecting group mediated intramolecular aglycon delivery: optimisation of mixed acetal formation and mechanistic investigation

  摘要：

  An efficient protocol for the formation of alpha-iodo mixed acetals, the first step of allyl-mediated 1AD, by reaction of allyl-derived enol ethers and alcohols, using I-2, AgOTf and di-tert-butyl methylpyridine as a novel source of I+, is reported. This reagent combination is capable of tethering glycosyl donors to the secondary alcohol groups of a variety of glycosyl acceptors including mono-, di- and trisaccharides. Mechanistic studies confirm the intramolecular nature of the glycosylation reaction, whilst the attempted use of diol glycosyl acceptors reveals limitations of both regio- and stereo selectivity in the glycosylation step. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.09.003
• 作为产物：
  描述：

  3,4,6-三-O-苄基-beta-D-吡喃甘露糖-1,2-(甲基原乙酸酯) 在 sodium hydride 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 75.0h， 生成 para-tolyl 2-O-allyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Allyl protecting group mediated intramolecular aglycon delivery: optimisation of mixed acetal formation and mechanistic investigation

  摘要：

  An efficient protocol for the formation of alpha-iodo mixed acetals, the first step of allyl-mediated 1AD, by reaction of allyl-derived enol ethers and alcohols, using I-2, AgOTf and di-tert-butyl methylpyridine as a novel source of I+, is reported. This reagent combination is capable of tethering glycosyl donors to the secondary alcohol groups of a variety of glycosyl acceptors including mono-, di- and trisaccharides. Mechanistic studies confirm the intramolecular nature of the glycosylation reaction, whilst the attempted use of diol glycosyl acceptors reveals limitations of both regio- and stereo selectivity in the glycosylation step. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.09.003