((2S,3R,4S)-3-Methoxy-2-methyl-6-oxo-tetrahydro-pyran-4-yl)-methyl-carbamic acid tert-butyl ester | 890122-81-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: ((2S,3R,4S)-3-Methoxy-2-methyl-6-oxo-tetrahydro-pyran-4-yl)-methyl-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S,3R,4S)-3-methoxy-2-methyl-6-oxooxan-4-yl]-N-methylcarbamate
• CAS: 890122-81-3
• 化学式: C₁₃H₂₃NO₅
• 分子量: 273.329
• InChiKey: LRDAPVRFXJTSKT-QXEWZRGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  呋喃-2-基-锂 、 ((2S,3R,4S)-3-Methoxy-2-methyl-6-oxo-tetrahydro-pyran-4-yl)-methyl-carbamic acid tert-butyl ester 在 吡啶 、 4-二甲氨基吡啶 、 三氟乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以92%的产率得到(2S,3S,4S)-[6-(furan-2-yl)-3-methoxy-2-methyl-3,4-dihydro-2H-pyran-4yl]methylcarbamic acid tert-butyl ester
  参考文献：
  名称：

  Facile synthesis of C-aryl glycals from sugar-derived lactones

  摘要：

  A general entry to C(I) aryl-substituted glycals from the corresponding sugar lactones is described. This approach features one-pot access to aryl glycals. A variety of aryllithium reagents can be used and the method is compatible with various 2-deoxysugar lactones. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.150
• 作为产物：
  描述：

  benzyl 3-azido-2,3,6-trideoxy-α-L-arabino-hexopyranoside 在 palladium on activated charcoal lithium aluminium tetrahydride 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 A molecular sieve 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 93.0h， 生成 ((2S,3R,4S)-3-Methoxy-2-methyl-6-oxo-tetrahydro-pyran-4-yl)-methyl-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Facile synthesis of C-aryl glycals from sugar-derived lactones

  摘要：

  A general entry to C(I) aryl-substituted glycals from the corresponding sugar lactones is described. This approach features one-pot access to aryl glycals. A variety of aryllithium reagents can be used and the method is compatible with various 2-deoxysugar lactones. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.150

文献信息

• Facile synthesis of C-aryl glycals from sugar-derived lactones
  作者：Hui Li、Kristen Procko、Stephen F. Martin

  DOI：10.1016/j.tetlet.2006.02.150

  日期：2006.5

  A general entry to C(I) aryl-substituted glycals from the corresponding sugar lactones is described. This approach features one-pot access to aryl glycals. A variety of aryllithium reagents can be used and the method is compatible with various 2-deoxysugar lactones. (c) 2006 Elsevier Ltd. All rights reserved.