(+)-(2R,3R)-3-(2-Furyl)-1,2-O-isopropylidene-3-methoxypropane | 151867-34-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(2R,3R)-3-(2-Furyl)-1,2-O-isopropylidene-3-methoxypropane
• 英文别名: (4R)-4-[(R)-furan-2-yl(methoxy)methyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 151867-34-4
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: PKCQCMYAYPPSDG-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-(2R,3R)-3-(2-Furyl)-1,2-O-isopropylidene-3-methoxypropane 在 ruthenium(IV) oxide 、 sodium periodate 、 三氟甲磺酸 、 碳酸氢钠 、 三氟乙酸 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 二氯甲烷 、 环己烷 、 水 、 乙腈 为溶剂， 反应 3.0h， 生成 (-)-(2R,3R)-3-Benzyloxy-4-hydroxy-2-methoxybutanoic 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：

  2,2-dimethyl-4-(2-furyl)hydroxymethyl-1,3-dioxolane 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.42h， 以87%的产率得到(+)-(2R,3R)-3-(2-Furyl)-1,2-O-isopropylidene-3-methoxypropane
  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.