Benzoic acid (1R,2S,4R,5R,6R)-4-(3-ethoxycarbonyl-but-3-enyl)-2-methoxy-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester | 182312-62-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzoic acid (1R,2S,4R,5R,6R)-4-(3-ethoxycarbonyl-but-3-enyl)-2-methoxy-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester
• 英文别名: [(1R,2S,4R,5R,6R)-4-(3-ethoxycarbonylbut-3-enyl)-2-methoxy-3,7-dioxabicyclo[4.1.0]heptan-5-yl] benzoate
• CAS: 182312-62-5
• 化学式: C₂₀H₂₄O₇
• 分子量: 376.406
• InChiKey: WKNGCLIBUHWKPP-RXFYRGCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Benzoic acid (1R,2S,4R,5R,6R)-4-(3-ethoxycarbonyl-but-3-enyl)-2-methoxy-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以84%的产率得到4-((1R,2S,4R,5R,6R)-5-Hydroxy-2-methoxy-3,7-dioxa-bicyclo[4.1.0]hept-4-yl)-2-methylene-butyric acid ethyl ester
  参考文献：
  名称：

  C-Allylation of 1- and 6-Bromosugars with Allylic Sulfides and Sulfones

  摘要：

  Reaction of the bromosugars 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide (1), methyl 2,3-anhydro-6-bromo-6-deoxy-alpha-D-allopyranoside (2), and methyl 2,3-anhydro-4-O-benzoyl-6-bromo-6-deoxy-alpha-D-allopyranoside (3) with the-allylic sulfides and sulfones 4-9 in the presence of hexabutyldistannane under photolytic conditions gave the corresponding alpha-C-allyl galactosides 10-12 and the 6-C-allylated epoxysugars 13, 15, and 16 in 61-90% yield.

  DOI：

  10.1021/jo960749l
• 作为产物：
  描述：

  2,3-anhydro-4-O-benzoyl-6-bromo-6-deoxy-1-O-methyl-α-D-allopyranoside 、 乙基2-[(苯磺酰基)甲基]丙烯酸酯 在 六正丁基二锡 作用下， 以 苯 为溶剂， 反应 11.0h， 以70%的产率得到Benzoic acid (1R,2S,4R,5R,6R)-4-(3-ethoxycarbonyl-but-3-enyl)-2-methoxy-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester
  参考文献：
  名称：

  C-Allylation of 1- and 6-Bromosugars with Allylic Sulfides and Sulfones

  摘要：

  Reaction of the bromosugars 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide (1), methyl 2,3-anhydro-6-bromo-6-deoxy-alpha-D-allopyranoside (2), and methyl 2,3-anhydro-4-O-benzoyl-6-bromo-6-deoxy-alpha-D-allopyranoside (3) with the-allylic sulfides and sulfones 4-9 in the presence of hexabutyldistannane under photolytic conditions gave the corresponding alpha-C-allyl galactosides 10-12 and the 6-C-allylated epoxysugars 13, 15, and 16 in 61-90% yield.

  DOI：

  10.1021/jo960749l

文献信息

• C-Allylation of 1- and 6-Bromosugars with Allylic Sulfides and Sulfones
  作者：Fritiof Pontén、Göran Magnusson

  DOI：10.1021/jo960749l

  日期：1996.1.1

  Reaction of the bromosugars 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide (1), methyl 2,3-anhydro-6-bromo-6-deoxy-alpha-D-allopyranoside (2), and methyl 2,3-anhydro-4-O-benzoyl-6-bromo-6-deoxy-alpha-D-allopyranoside (3) with the-allylic sulfides and sulfones 4-9 in the presence of hexabutyldistannane under photolytic conditions gave the corresponding alpha-C-allyl galactosides 10-12 and the 6-C-allylated epoxysugars 13, 15, and 16 in 61-90% yield.