Erythromycin → Erythromycin A enol ether

HRID 1093927

반응식

HRID 1093927 반응식
[CH3:1][CH2:2][C@H:3]1[O:18][C:16](=[O:17])[C@H:15]([CH3:19])[C@@H:14]([O:20][C@@H:21]2[O:26][C@@H:25]([CH3:27])[C@H:24]([OH:28])[C@@:23]([O:30][CH3:31])([CH3:29])[CH2:22]2)[C@H:13]([CH3:32])[C@@H:12]([O:33][C@@H:34]2[O:39][C@H:38]([CH3:40])[CH2:37][C@H:36]([N:41]([CH3:43])[CH3:42])[C@H:35]2[OH:44])[C@@:11](O)([CH3:45])[CH2:10][C@@H:9]([CH3:47])[C:7](=[O:8])[C@H:6]([CH3:48])[C@@H:5]([OH:49])[C@@:4]1([OH:51])[CH3:50]>C(O)(=O)C>[CH3:1][CH2:2][C@H:3]1[O:18][C:16](=[O:17])[C@H:15]([CH3:19])[C@@H:14]([O:20][C@@H:21]2[O:26][C@@H:25]([CH3:27])[C@H:24]([OH:28])[C@@:23]([O:30][CH3:31])([CH3:29])[CH2:22]2)[C@H:13]([CH3:32])[C@@H:12]([O:33][C@@H:34]2[O:39][C@H:38]([CH3:40])[CH2:37][C@H:36]([N:41]([CH3:42])[CH3:43])[C@H:35]2[OH:44])[C@:11]2([CH3:45])[O:8][C:7](=[C:9]([CH3:47])[CH2:10]2)[C@H:6]([CH3:48])[C@@H:5]([OH:49])[C@@:4]1([OH:51])[CH3:50]

참가 물질

3

반응물 1

HCID 12560Erythromycin2회

생성물 1

HCID 83954Erythromycin A enol ether

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

That is, according to references (a) I. O. Kibwage, R. Busson, G. Janssen, J. Hoogmartens, H. Vanderhaeghe, Translactonization of Erythromycins, J. Org. Chem., 52, 990-996, 1987, (b) H. A. Kirst, J. A. Wind, J. W. Paschal, Synthesis of Ring-Constracted Derivatives of Erythromycin, J. Org. Chem. 52, 4359-4362, 1987, erythromycin A was treated with glacial acetic acid to give 8,9-anhydroerythromycin A 6,9-hemiketal (EM201). Successively, the compound was heated under reflux in the presence of potassium carbonate in methanol to give 8,9-anhydro-pseudoerythromycin A 6,9-hemiketal (EM701).

출처 및 근거

ORD 기록
ord-b095d68ae3984f998e1ce0bb476ce8a9
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133871B2

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