Diisopropyl-carbamic acid (2R,3R,6R)-2-((S)-1-benzyloxy-ethyl)-6-methoxy-4-methylene-tetrahydro-pyran-3-yl ester | 854970-12-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Diisopropyl-carbamic acid (2R,3R,6R)-2-((S)-1-benzyloxy-ethyl)-6-methoxy-4-methylene-tetrahydro-pyran-3-yl ester
• 英文别名: [(2R,3R,6R)-6-methoxy-4-methylidene-2-[(1S)-1-phenylmethoxyethyl]oxan-3-yl] N,N-di(propan-2-yl)carbamate
• CAS: 854970-12-0
• 化学式: C₂₃H₃₅NO₅
• 分子量: 405.535
• InChiKey: RILURPLGKCWLEJ-BDKRGJGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Diisopropyl-carbamic acid (2R,3R,6R)-2-((S)-1-benzyloxy-ethyl)-6-methoxy-4-methylene-tetrahydro-pyran-3-yl ester 在 三氟甲磺酸三甲基硅酯 、 potassium acetate 、 对甲苯磺酰肼 作用下， 以 乙腈 为溶剂， 生成 Diisopropyl-carbamic acid (2R,3R,6R)-2-((S)-1-benzyloxy-ethyl)-4-methylene-6-propyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of highly substituted 2,6-anti-configured tetrahydropyrans. First steps towards an efficient access to amphidinol 3 ring system

  摘要：

  Highly functionalised and polysubstituted tetrahydropyrans, akin to the middle core of the amphidinols, can be efficiently synthesised, with full stereocontrol and in good yields, using as key steps an anti-allylation reaction coupled with an intramolecular Sakurai cyclisation. Three approaches were devised in order to reach a broad range of substitution patterns. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.041
• 作为产物：
  描述：

  原甲酸三甲酯 、 (3R,4R,5S)-5-(benzyloxy)-4-hydroxy-2-((trimethylsilyl)methyl)hex-1-en-3-yl diisopropylcarbamate 在 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到Diisopropyl-carbamic acid (2R,3R,6R)-2-((S)-1-benzyloxy-ethyl)-6-methoxy-4-methylene-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of highly substituted 2,6-anti-configured tetrahydropyrans. First steps towards an efficient access to amphidinol 3 ring system

  摘要：

  Highly functionalised and polysubstituted tetrahydropyrans, akin to the middle core of the amphidinols, can be efficiently synthesised, with full stereocontrol and in good yields, using as key steps an anti-allylation reaction coupled with an intramolecular Sakurai cyclisation. Three approaches were devised in order to reach a broad range of substitution patterns. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.041