erythromycin A

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: erythromycin A
• 英文别名: erythromycin；(3R,4S,5S,6R,7S,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
• 化学式: C₃₇H₆₇NO₁₃
• 分子量: 733.938
• InChiKey: ULGZDMOVFRHVEP-TVTZEDOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  51
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  194
• 氢给体数：
  5
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  erythromycin A 在 potassium tert-butylate 作用下， 生成
  参考文献：
  名称：

  The synthesis of ketolide antibiotic ABT-773 (cethromycin)

  摘要：

  A practical and efficient synthesis of ketolide antibiotic cethromycin (ABT-773) (1) is described. An effective protection strategy allows high yielding, regioselective C6-O-alkylation and subsequent stereoselective modification of the erythromycin nucleus. ABT-773 was prepared in 10 steps from commercially available erythromycin A oxime. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.027

文献信息

• [EN] ANTIMICROBIAL DERIVATIVES<br/>[FR] DERIVES ANTIMICROBIENS
  申请人：CHIRON CORP

  公开号：WO2005028493A1

  公开（公告）日：2005-03-31

  Antimicrobial compounds are provided having the formula (Q): as well as tautomers, stereoisomers, pharmaceutically acceptable salts, esters or prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of the compounds.

  提供具有公式（Q）的抗微生物化合物，以及其互变异构体、立体异构体、药学上可接受的盐、酯或前药；包含此类化合物的药物组合物；通过给予这种化合物进行治疗细菌感染的方法；以及制备这种化合物的过程。
• Process for producing erythromycin derivative
  申请人：——

  公开号：US20030191295A1

  公开（公告）日：2003-10-09

  There is provided a preparation process useful for an efficient synthesis of 6-O-substituted ketolide derivatives by combining a characterized step of introduction of a substituent at the 6-position by selective cleavage of a C—O bond of the cyclic acetal at the 9-position side via 6,9-cyclic acetal 5-O-desosaminyl erythronolide derivative, a step of conversion into carbonyl groups at the 9- and 3-positions, and a step of 11,12-cyclic carbamation to lead to 6-O-substituted ketolide derivatives.

  提供了一种制备过程，可通过将在9位侧的6,9-环缩醛5-O-去甲胺基红霉素衍生物的C-O键选择性断裂的特征步骤与将9位和3位转化为羰基的步骤以及11,12-环状碳酰胺化的步骤结合起来，高效地合成6-O取代的酮酸类衍生物。
• Synthetic studies of erythromycin derivatives: 6-O-methylation of (9S)-12,21-anhydro-9-dihydroerythromycin A derivatives
  作者：Wei-Min Chen、Henry N.C Wong、Daniel T.W Chu、Xiaodong Lin

  DOI：10.1016/s0040-4020(03)00817-2

  日期：2003.8

  Synthetic studies on methylation of erythromycin derivatives were conducted. Methylation of 6 resulted in the formation of the C-3′ quaternary ammonium salts with a rate faster than 6-O-methylation. In dipolar aprotic solvent and under strong base conditions, 6-O-methylation, C-3′ quaternary ammonium salts formation and 2-C-methylation proceeded simultaneously to yield a mixture of three different

  进行了红霉素衍生物甲基化的合成研究。甲基化6导致形成C-3'季铵盐，其速率快于6- O-甲基化。在偶极非质子溶剂和强碱的条件下，将6- ö -methylation，C-3'季铵盐形成和2- Ç -methylation同时进行，以产生三个不同的产物的混合物7，8和9。季铵盐转化回相应的叔胺2，10和起始材料6通过采用钠-4-基吡啶作为N-脱甲基试剂。6- Ô -methylation最终以高收率获得当苄氧羰基（Cbz）基团被用于保护Ç -3'-二甲基氨基的4。在此报告中，我们将讨论（9 S）-12、21-脱水-9-二氢红霉素A衍生物的甲基化过程中不同反应过程的细节。
• Chemical modification of erythromycin: Novel reaction observed by treatment with metalloporphyrins
  作者：Joseph E. Celebuski、Mukund S. Chorghade、Elaine C. Lee

  DOI：10.1016/s0040-4039(00)76680-9

  日期：1994.6

  Reaction of erythromycin and other macrolides with metalloporphyrins and exogenous co-oxidants leads to replacement of the N-dimethyl moiety in the desosamine sugar with complete retention of configuration. The resulting macrolides show antibacterial activity.

  红霉素和其他大环内酯类化合物与金属卟啉和外源性共氧化剂的反应导致脱氨糖中N-二甲基部分的置换，并完全保留了构型。所得的大环内酯类化合物显示抗菌活性。
• Stereoselective Deoxygenation of Erythromycin A at C-12: Effect of Structure and Conformation on Prokinetic Activity.
  作者：PAUL A. LARTEY、RAMIN FAGHIH、THOMAS PAGANO、HUGH N. NELLANS、ALBERT PETERSEN、JACOB J. PLATTNER

  DOI：10.7164/antibiotics.48.730

  日期：——