(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-methoxy-acetic acid | 151867-35-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-methoxy-acetic acid
• 英文别名: (2R)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methoxyacetic acid
• CAS: 151867-35-5
• 化学式: C₈H₁₄O₅
• 分子量: 190.196
• InChiKey: VEAOCERMSUNHQU-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.24
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-methoxy-acetic acid 在 三氟甲磺酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 环己烷 、 水 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 在 ruthenium(IV) oxide 、 sodium periodate 、 sodium hydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 乙腈 为溶剂， 反应 0.42h， 生成 (R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-methoxy-acetic acid
  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