benzyl 2-acetamido-2-deoxy-3-O-(p-fluorophenyloxythiocarbonyl)-4,6-O-isopropylidene-α-D-glucopyranoside | 716377-16-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: benzyl 2-acetamido-2-deoxy-3-O-(p-fluorophenyloxythiocarbonyl)-4,6-O-isopropylidene-α-D-glucopyranoside
• 英文别名: N-[(4aR,6S,7R,8R,8aS)-8-(4-fluorophenoxy)carbothioyloxy-2,2-dimethyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• CAS: 716377-16-1
• 化学式: C₂₅H₂₈FNO₇S
• 分子量: 505.564
• InChiKey: TYSDTLVWJGKRCB-JLMDMGSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tributyl(2,4-pentadienyl)stannane 、 benzyl 2-acetamido-2-deoxy-3-O-(p-fluorophenyloxythiocarbonyl)-4,6-O-isopropylidene-α-D-glucopyranoside 在 偶氮二异丁腈 作用下， 以 甲苯 为溶剂， 生成 benzyl 2-acetamido-2,3-dideoxy-4,6-O-isopropylidene-3-C-(penta-2',4'-dienyl)-α-D-glucopyranoside 、 benzyl 2-acetamido-2,3-dideoxy-4,6-O-isopropylidene-3-C-(penta-2',4'-dienyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of C‐3 Branched Allyl and Pentadienyl Glucosamines via Radical Coupling of Sugar‐Thionocarbonates

  摘要：

  The intermolecular AIBN-promoted free radical reaction of glucosamine thionocarbonates as radical donors, and allyl or pentadienyl-tributyltin reagents gave the expected C-3 branched sugar derivatives in good yield and with total equatorial selectivity.

  DOI：

  10.1081/car-120030469
• 作为产物：
  描述：

  4-氟苯基氯硫代甲酸酯 、 苄基(5Xi)-2-乙酰氨基-2-脱氧-4,6-O-异亚丙基-alpha-D-来苏-吡喃己糖苷 在 吡啶 作用下， 反应 12.0h， 以100%的产率得到benzyl 2-acetamido-2-deoxy-3-O-(p-fluorophenyloxythiocarbonyl)-4,6-O-isopropylidene-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of C‐3 Branched Allyl and Pentadienyl Glucosamines via Radical Coupling of Sugar‐Thionocarbonates

  摘要：

  The intermolecular AIBN-promoted free radical reaction of glucosamine thionocarbonates as radical donors, and allyl or pentadienyl-tributyltin reagents gave the expected C-3 branched sugar derivatives in good yield and with total equatorial selectivity.

  DOI：

  10.1081/car-120030469

文献信息

• Synthesis of <i>C</i>‐3 Branched Allyl and Pentadienyl Glucosamines via Radical Coupling of Sugar‐Thionocarbonates
  作者：Qian Wan、André Lubineau、Marie‐Christine Scherrmann

  DOI：10.1081/car-120030469

  日期：2004.12.26

  The intermolecular AIBN-promoted free radical reaction of glucosamine thionocarbonates as radical donors, and allyl or pentadienyl-tributyltin reagents gave the expected C-3 branched sugar derivatives in good yield and with total equatorial selectivity.