- Evaluation of the efficiency of the macrolactonization using MNBA in the synthesis of erythromycin a aglycon
-
Various intermediates for the synthesis of erythronolide A, an aglycon of erythromycin A, are prepared from the corresponding seco-acids using 2-methyl-6-nitrobenzoic anhydride (MNBA) in the presence of 4-(dimethylamino)pyridine (DMAP) with or without tri
- Shiina, Isamu,Katoh, Takashi,Nagai, Shunsuke,Hashizume, Minako
-
scheme or table
p. 305 - 320
(2011/02/22)
-
- PREPARATION AND UTILITY OF SUBSTITUTED ERYTHROMYCIN ANALOGS
-
The present disclosure is directed to novel macrolide antibiotics of Formula 1 and pharmaceutically acceptable salts and prodrugs thereof; and the chemical syntheses and medical uses of these novel macrolide antibiotics for the treatment and/or management of infections caused by various aerobic and anaerobic gram-positive and gram-negative microorganisms as well as various mycobacteria.
- -
-
Page/Page column 28; 31
(2008/06/13)
-
- Method of preparing clarithromycin
-
Clarithromycin can be easily prepared by reacting erythromycin A N-oxide with a methylating agent to obtain 6-O-methylerythromycin A N-oxide; and treating 6-O-methylerythromycin A N-oxide obtained above with a reducing agent in a high yield.
- -
-
Page column 5
(2010/02/08)
-
- Preparation of (8S)-8-fluoroerythromycins with N-F fluorinating agents
-
(8S)-8-fluoroerythromycins are prepared by reacting 8,9-anhydroerythromycin 6,9-hemiacetals or an N-oxide thereof with a carboxylic acid and an N-F fluorinating agent. The anhydro starting material may be prepared in situ from erythromycins or an N-oxide
- -
-
-
- SYNTHESIS OF ERYTHROMYCIN RELATED MACROLIDES
-
The synthesisand characterization of a number of macrolides, structurally related with erythromycin, is described.These derivatives have been previously investigated for thier ability to induce contractions and to displace bound motilin in rabbit duodenum.
- Paesen, Jos,Roets, Eugene,Janssen, Gerard,Busson, Roger,Cachet, Thierry,Hoogmartens, Jos
-
p. 205 - 212
(2007/10/03)
-
- Application of highly stereocontrolled glycosidations employing 2,6-anhydro-2-thio sugars to the syntheses of erythromycin A and olivomycin A trisaccharide
-
The highly efficient syntheses of the erythromycin A (1) from its aglycon, (9S)-9-dihydroerythronolide A (4), and the C-D-E trisaccharide 3 of olivomycin A have been accomplished by the successful application of stereocontrolled glycosidations using 2,6-anhydro-2-thio sugars. The former synthesis includes the highly α-stereoselective glycosidation of the C5 desosaminated lactone 12 with phenyl 2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-1,2-dithio-L-altropyranos ide (10), which was achieved by using NIS-TfOH. The latter synthesis involves both the highly β-stereoselective glycosidation of 1,3-di-O-acetyl-2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranose (23), which was realized by employing TMSOTf, and the highly α-stereoselective glycosidation of phenyl 2,6-anhydro-3-O-(diethylisopropylsilyl)-4-O-isobutyryl-3-C-methyl- 1,2-dithio-L-manno-pyranoside (24), which succeeded by utilizing NBS. Hydrogenolyses using Raney Ni as a catalyst and selective deprotections of the key glyco substances 17 and 22 led to the total syntheses of erythromycin A (1) and the C-D-E trisaccharide 3 of olivomycin A, respectively.
- Toshima, Kazunobu,Nozaki, Yuko,Mukaiyama, Satsuki,Tamai, Tetsuro,Nakata, Masaya,Tatsuta, Kuniaki,Kinoshita, Mitsuhiro
-
p. 3717 - 3727
(2007/10/02)
-
- Application of efficient glycosylation of 2,6-anhydro-2-thio sugar to the total synthesis of erythromycin A
-
The total synthesis of erythromycin A (1) from (9S)-9-dihydroerythronolide A (2) was achieved efficiently by the highly stereoselective and powerful glycosylation of 2,6-anhydro-2-thio sugar 9 as a key step.
- Toshima,Mukaiyama,Yoshida,Tamai,Tatsuta
-
p. 6155 - 6158
(2007/10/02)
-
