Реакция #1435738

ord-a8e7b5bcc1c24025ae3c1b39599ac2cd

Уравнение реакции

CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O
erythromycin A
[BH4-].[Na+]
NaBH4
→
CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@]1(C)O
product
Выход 58.0%
CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@]1(C)O
(9S)-9-Dihydroerythromycin A
Выход 58.0%

Реактанты

CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O
erythromycin A
[BH4-].[Na+]
NaBH4

Реагенты

Нет

Растворители

C1CCOC1
THF

Условия реакции

Температура
0°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Другоеwas quenched with water
  2. 2
    ДругоеAfter evaporation of the majority of the solvent, dilute NaHCO3 solution
  3. 3
    workup.ADDITIONwas added
  4. 4
    Экстракцияthe mixture was extracted three times with EtOAc
  5. 5
    ПромывкаThe combined organic layers were washed with water and brine
  6. 6
    Сушкаdried over MgSO4
  7. 7
    ДругоеThe crude product was purified by silica gel chromatography

Методика

To a solution of erythromycin A (22.0 g, 30 mmol) in THF (200 mL) cooled to −10° C. was added NaBH4 (2.27 g, 60 mmol) in small portions. The mixture was then allowed to stir at 0° C. for 3 h before the reaction was quenched with water. After evaporation of the majority of the solvent, dilute NaHCO3 solution was added, the mixture was extracted three times with EtOAc. The combined organic layers were washed with water and brine, dried over MgSO4. The crude product was purified by silica gel chromatography using 2:1 hexane-acetone with 1% Et3N to give pure product (12.8 g, 58% yield). m/z: 736.5 (MH); 13C-NMR (CDCl3): 177.00, 103.21, 96.32, 84.20, 83.10, 79.23, 77.72, 77.63, 74.99, 74.48, 72.66, 70.75, 70.69, 69.29, 66.09, 65.02, 49.32, 45.52, 41.73, 40.32 (2×), 36.91, 34.84, 34.23, 31.97, 28.81, 25.25, 21.68, 21.51, 21.18, 20.06, 18.12, 16.50, 15.06, 14.80, 10.81, 9.36.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US07211568B2uspto-grants-2007_05