(2S,3R,4R)-4-acetoxy-4-hydroxy-2-<(1R)-1-hydroxyethyl>-2,3-dimethylbutanoic acid γ-lactone | 141585-63-9

• 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,4R)-4-acetoxy-4-hydroxy-2-<(1R)-1-hydroxyethyl>-2,3-dimethylbutanoic acid γ-lactone
• 英文别名: [(2R,3R,4S)-4-[(1R)-1-hydroxyethyl]-3,4-dimethyl-5-oxooxolan-2-yl] acetate
• CAS: 141585-63-9
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: QNXMFQPMRPSHPV-NSSITKEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R)-4-acetoxy-4-hydroxy-2-<(1R)-1-hydroxyethyl>-2,3-dimethylbutanoic acid γ-lactone 在 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以92%的产率得到(-)-4-epi-acetomycin
  参考文献：
  名称：

  Total syntheses of (-)-acetomycin and its three stereoisomers at C-4 and C-5

  摘要：

  The total synthesis of the antitumor and antimicrobial agent (-)-acetomycin (1) from the previously reported tetrahydrofuran 10, a derivative Of D-glucose is described. Reactions which altered only the side chains of 10 gave the substituted tetrahydrofuran 20, which was then converted into the acyclic alcohol 38 and oxidized to the corresponding carboxylic acid 39. Ozonolysis of the vinyl group of 39 gave an aldehyde, spontaneous cyclization of which afforded a 5:1 mixture of the diastereomeric gamma-hydroxy gamma-lactone 40. Treatment of the mixture with acetic anhydride in pyridine gave predominantly (>45:1) the alpha-acetate 41. On the other hand, treatment of compounds 40 with methanesulfonyl chloride/triethylamine in benzene, followed by treatment of the mixture of mesylates so formed with silver acetate and tetrabutylammonium acetate, resulted in the formation of a 1.3:1 mixture of 41 and the beta-acetate 42. Removal of the MOM protecting group of 41 and 42 and pyridinium chlorochromate (PCC) oxidation of the products gave (+)-5-epi-acetomycin (2) and 1, respectively. In a similar manner, (-)-4-epi-acetomycin (3) and (+)-4,5-di-epi-acetomycin (4) were synthesized from the substituted tetrahydrofuran 11. The results of preliminary studies of the in vitro inhibitory effects of compounds 2-4 on the growth of several tumor cells are also presented.

  DOI：

  10.1021/jo00040a014
• 作为产物：
  描述：

  (R)-2-((3aR,5R,6S,6aR)-2,2,5,6-Tetramethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-propionaldehyde 在 吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 三甲基溴硅烷 、 4 A molecular sieve 、 Jones's reagent 、 臭氧 、 N,N-二异丙基乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 125.5h， 生成 (2S,3R,4R)-4-acetoxy-4-hydroxy-2-<(1R)-1-hydroxyethyl>-2,3-dimethylbutanoic acid γ-lactone
  参考文献：
  名称：

  Total syntheses of (-)-acetomycin and its three stereoisomers at C-4 and C-5

  摘要：

  The total synthesis of the antitumor and antimicrobial agent (-)-acetomycin (1) from the previously reported tetrahydrofuran 10, a derivative Of D-glucose is described. Reactions which altered only the side chains of 10 gave the substituted tetrahydrofuran 20, which was then converted into the acyclic alcohol 38 and oxidized to the corresponding carboxylic acid 39. Ozonolysis of the vinyl group of 39 gave an aldehyde, spontaneous cyclization of which afforded a 5:1 mixture of the diastereomeric gamma-hydroxy gamma-lactone 40. Treatment of the mixture with acetic anhydride in pyridine gave predominantly (>45:1) the alpha-acetate 41. On the other hand, treatment of compounds 40 with methanesulfonyl chloride/triethylamine in benzene, followed by treatment of the mixture of mesylates so formed with silver acetate and tetrabutylammonium acetate, resulted in the formation of a 1.3:1 mixture of 41 and the beta-acetate 42. Removal of the MOM protecting group of 41 and 42 and pyridinium chlorochromate (PCC) oxidation of the products gave (+)-5-epi-acetomycin (2) and 1, respectively. In a similar manner, (-)-4-epi-acetomycin (3) and (+)-4,5-di-epi-acetomycin (4) were synthesized from the substituted tetrahydrofuran 11. The results of preliminary studies of the in vitro inhibitory effects of compounds 2-4 on the growth of several tumor cells are also presented.

  DOI：

  10.1021/jo00040a014