醋霉素 | 510-18-9

• 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
• 中文名称: 醋霉素
• 英文名称: (-)-Acetomycin
• 英文别名: Acetomycin；[(2R,3S,4S)-4-acetyl-3,4-dimethyl-5-oxooxolan-2-yl] acetate
• CAS: 510-18-9
• 化学式: C₁₀H₁₄O₅
• 分子量: 214.218
• InChiKey: OYMZTORLGBISLR-RHFNHBFPSA-N

物化性质

• 熔点：
  115-116℃ (methanol )
• 沸点：
  336.2±42.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO：可溶，甲醇：可溶

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

安全信息

• 海关编码：
  2932190090

反应信息

• 作为产物：
  描述：

  (-)-5-(R)-acetoxy-4-methyl-2(5H)-furanone 在 palladium on activated charcoal Rany nickel 、 氢气 、 lithium hexamethyldisilazane 作用下， 以 甲醇 、 乙醇 、 丙酮 为溶剂， 反应 15.72h， 生成 醋霉素
  参考文献：
  名称：

  Asymmetric synthesis of acetomycin

  摘要：

  The synthesis of (-)-acetomycin 1, a highly functionalized gamma-lactone with antitumor activity, was achieved in five steps with nearly complete enantioselectivity. The key step was realized by a large scale lipase R catalyzed esterification of 5-hydroxy-4-methyl-2(5H)-furanone 2 providing (-)-(5R)-5-acetoxy-4-methyl-2(5H)-furanone 3 with an e.e., of 99%. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00100-1

文献信息

• Construction of Consecutive Chiral Non-Racemic Quaternary and Tertiary Carbon Centers: A Short Synthetic Route to (−)-Acetomycin
  作者：Jun′ichi Uenishi、Motoi Kawatsura、Daiji Ikeda、Nobuhiro Muraoka

  DOI：10.1002/ejoc.200300504

  日期：2003.10

  substitution of 2-methylacetoacetate with a chiral non-racemic π-allyl Pd complex creates consecutive chiral non-racemic quaternary and tertiary carbon centers. σ-Bond formation between the re-face of the π-allyl Pd complex and the re-face of the enol acetoacetate was controlled by the o-(diphenylphosphanyl)arylcarboxylic acid ligand selectively. (−)-Acetomycin was synthesized in seven steps using this

  2-乙酰乙酸甲酯与手性非外消旋 π-烯丙基 Pd 络合物的区域和非对映选择性亲核取代产生连续的手性非外消旋季碳和叔碳中心。π-烯丙基钯配合物的表面与烯醇乙酰乙酸酯的表面之间的σ-键形成受邻-（二苯基膦基）芳基羧酸配体的选择性控制。(-)-Acetomycin 是使用这种关键方法分七个步骤合成的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• A selective baeyer-villiger oxidation: A total synthesis of (−)-Acetomycin
  作者：Frederick E. Ziegler、Hakwon Kim

  DOI：10.1016/s0040-4039(00)61535-6

  日期：1993.11
• 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
• 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.
• Asymmetric synthesis of acetomycin
  作者：Sape S Kinderman、Ben L Feringa

  DOI：10.1016/s0957-4166(98)00100-1

  日期：1998.4

  The synthesis of (-)-acetomycin 1, a highly functionalized gamma-lactone with antitumor activity, was achieved in five steps with nearly complete enantioselectivity. The key step was realized by a large scale lipase R catalyzed esterification of 5-hydroxy-4-methyl-2(5H)-furanone 2 providing (-)-(5R)-5-acetoxy-4-methyl-2(5H)-furanone 3 with an e.e., of 99%. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.