(+)-5-epi-Acetomycin | 141660-81-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+)-5-epi-Acetomycin
• 英文别名: [(2S,3S,4S)-4-acetyl-3,4-dimethyl-5-oxooxolan-2-yl] acetate
• CAS: 141660-81-3
• 化学式: C₁₀H₁₄O₅
• 分子量: 214.218
• InChiKey: OYMZTORLGBISLR-OOSDCERQSA-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：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2S,3S,4R)-4-acetoxy-4-hydroxy-2-<(1R)-(methoxymethoxy)ethyl>-2,3-dimethylbutanoic acid γ-lactone 在 molecular sieve 三甲基溴硅烷 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 (+)-5-epi-Acetomycin
  参考文献：
  名称：

  Total synthesis of (−)-acetomycin

  摘要：

  DOI：

  10.1016/0040-4039(90)80138-c

文献信息

• Formation of Chiral Quaternary Carbon Stereocenters Using Silylene Transfer Reactions:  Enantioselective Synthesis of (+)-5-<i>epi</i>-Acetomycin
  作者：Stacie A. Calad、K. A. Woerpel

  DOI：10.1021/ol063072p

  日期：2007.3.1

  Chiral quaternary carbon stereocenters can be established with high diastereoselectivity by a silylene transfer/Ireland-Claisen rearrangement. The utility of this method was demonstrated by application to a synthesis of (+)-5-epi-acetomycin. [reaction: see text]

  可以通过甲硅烷基转移/爱尔兰-克莱森重排以高非对映选择性建立手性季碳立体中心。该方法的实用性通过应用于合成（+）-5-表霉素。[反应：看文字]
• Total synthesis of (−)-acetomycin
  作者：Kin-ichi Tadano、Jun Ishihara、Seiichiro Ogawa

  DOI：10.1016/0040-4039(90)80138-c

  日期：1990.1
• TADANO, KIN-ICHI;ICHIHARA, JUN;OGAWA, SEIICHIRO, TETRAHEDRON LETT., 31,(1990) N8, C. 2609-2612
  作者：TADANO, KIN-ICHI、ICHIHARA, JUN、OGAWA, SEIICHIRO

  DOI：——

  日期：——
• Total syntheses of (-)-acetomycin and its three stereoisomers at C-4 and C-5
  作者：Jun Ishihara、Kyoko Tomita、Kinichi Tadano、Seiichiro Ogawa

  DOI：10.1021/jo00040a014

  日期：1992.7

  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.