para-tolyl 2-O-allyl-(R)-4,6-O-benzylidene-3-O-pivaloyl-1-thio-α-D-mannopyranoside | 807333-78-4

• 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-(R)-4,6-O-benzylidene-3-O-pivaloyl-1-thio-α-D-mannopyranoside
• 英文别名: [(2R,4aR,6R,7S,8S,8aR)-6-(4-methylphenyl)sulfanyl-2-phenyl-7-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 2,2-dimethylpropanoate
• CAS: 807333-78-4
• 化学式: C₂₈H₃₄O₆S
• 分子量: 498.64
• InChiKey: JTZZJEVTLCLITD-PSRUHSIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  para-tolyl 2-O-allyl-(R)-4,6-O-benzylidene-3-O-pivaloyl-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 (R)-4,6-O-benzylidene-3-O-pivaloyl-2-O-(prop-1-enyl)-1-thio-α-D-mannopyranoside 、 para-tolyl (R)-4,6-O-benzylidene-3-O-pivaloyl-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：

  4-METHYLPHENYL2,3,4,6-TETRA-O-ACETYL-1-THIO-Α-D-MANNOPYRANOSIDE4-甲基苯基2,3,4,6-四-O-乙酰基-1-硫代-Α-D-吡喃甘露糖苷 在 吡啶 、 甲醇 、 camphor-10-sulfonic acid 、 sodium 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、999.92 Pa 条件下， 反应 14.17h， 生成 para-tolyl 2-O-allyl-(R)-4,6-O-benzylidene-3-O-pivaloyl-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

文献信息

• Allyl protecting group mediated intramolecular aglycon delivery: optimisation of mixed acetal formation and mechanistic investigation
  作者：Ian Cumpstey、Kampanart Chayajarus、Antony J. Fairbanks、Alison J. Redgrave、Christopher M.P. Seward

  DOI：10.1016/j.tetasy.2004.09.003

  日期：2004.10

  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.