(-)-(2R,3R,4S,5R,E)-3-(Benzyloxy)-4-hydroxy-2-methoxy-8-methyl-5-(methoxymethoxy)-6-nonenoic acid 1,4-lactone | 146383-97-3

• 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: (-)-(2R,3R,4S,5R,E)-3-(Benzyloxy)-4-hydroxy-2-methoxy-8-methyl-5-(methoxymethoxy)-6-nonenoic acid 1,4-lactone
• 英文别名: (3R,4R,5S)-3-methoxy-5-[(E,1R)-1-(methoxymethoxy)-4-methylpent-2-enyl]-4-phenylmethoxyoxolan-2-one
• CAS: 146383-97-3
• 化学式: C₂₀H₂₈O₆
• 分子量: 364.439
• InChiKey: AJALNNPTDUXRRO-UJHDDLGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-(2R,3R,4S,5R,E)-3-(Benzyloxy)-4-hydroxy-2-methoxy-8-methyl-5-(methoxymethoxy)-6-nonenoic acid 1,4-lactone 在 吡啶 、 lithium tetrafluoroborate 、 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 80.0h， 生成 (-)-(2R,3R,4S,5R,E)-3,5-Diacetoxy-4-hydroxy-2-methoxy-8-methyl-6-nonenoic acid 1,4-lactone
  参考文献：
  名称：

  Stereoselective total synthesis of bengamide E from glyceraldehyde acetonide and a nonracemic .gamma.-alkoxy allylic stannane

  摘要：

  The synthesis of bengamide E (30) was achieved starting from the furan adduct 1 of (R)-glyceraldehyde acetonide. The key step entailed MgBr2-promoted addition of the (S)-gamma-alkoxy allylic stannane (S)-25 to the aldehyde 8 obtained from the oxidation product of furan 1 after protection as the methyl ether. The adduct of stannane (S)-25 and aldehyde 8, a 1:1 mixture of hydroxy ester 27 and lactone 28 was converted to bengamide E by aminolysis with (S)-2-aminocaprolactam and subsequent debenzylation with Li in NH3.

  DOI：

  10.1021/jo00075a017
• 作为产物：
  描述：

  (+)-Methyl (2R,3R)-3-(benzyloxy)-4-hydroxy-2-methoxybutanoate 在 戴斯-马丁氧化剂 、 magnesium bromide 作用下， 以 二氯甲烷 为溶剂， 反应 49.33h， 生成 (-)-(2R,3R,4S,5R,E)-3-(Benzyloxy)-4-hydroxy-2-methoxy-8-methyl-5-(methoxymethoxy)-6-nonenoic acid 1,4-lactone
  参考文献：
  名称：

  Stereoselective total synthesis of bengamide E from glyceraldehyde acetonide and a nonracemic .gamma.-alkoxy allylic stannane

  摘要：

  The synthesis of bengamide E (30) was achieved starting from the furan adduct 1 of (R)-glyceraldehyde acetonide. The key step entailed MgBr2-promoted addition of the (S)-gamma-alkoxy allylic stannane (S)-25 to the aldehyde 8 obtained from the oxidation product of furan 1 after protection as the methyl ether. The adduct of stannane (S)-25 and aldehyde 8, a 1:1 mixture of hydroxy ester 27 and lactone 28 was converted to bengamide E by aminolysis with (S)-2-aminocaprolactam and subsequent debenzylation with Li in NH3.

  DOI：

  10.1021/jo00075a017

文献信息

• Stereoselective total synthesis of bengamide E from glyceraldehyde acetonide and a nonracemic .gamma.-alkoxy allylic stannane
  作者：James A. Marshall、George P. Luke

  DOI：10.1021/jo00075a017

  日期：1993.11

  The synthesis of bengamide E (30) was achieved starting from the furan adduct 1 of (R)-glyceraldehyde acetonide. The key step entailed MgBr2-promoted addition of the (S)-gamma-alkoxy allylic stannane (S)-25 to the aldehyde 8 obtained from the oxidation product of furan 1 after protection as the methyl ether. The adduct of stannane (S)-25 and aldehyde 8, a 1:1 mixture of hydroxy ester 27 and lactone 28 was converted to bengamide E by aminolysis with (S)-2-aminocaprolactam and subsequent debenzylation with Li in NH3.