8-epi-(S)-8a-aza-3'-N-demethyl-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)-8a-homoerythromycin A cyclic 11,12-carbonate

Base Information

• Chemical Name: 8-epi-(S)-8a-aza-3'-N-demethyl-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)-8a-homoerythromycin A cyclic 11,12-carbonate
• CAS No.: 488794-88-3
• Molecular Formula: C₆₁H₈₂N₂O₂₀
• Molecular Weight: 1163.32

Synonyms:8-epi-(S)-8a-aza-3'-N-demethyl-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)-8a-homoerythromycin A cyclic 11,12-carbonate

Chemical Property of 8-epi-(S)-8a-aza-3'-N-demethyl-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)-8a-homoerythromycin A cyclic 11,12-carbonate

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Technology Process of 8-epi-(S)-8a-aza-3'-N-demethyl-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)-8a-homoerythromycin A cyclic 11,12-carbonate

There total 10 articles about 8-epi-(S)-8a-aza-3'-N-demethyl-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)-8a-homoerythromycin A cyclic 11,12-carbonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 52.0%

3'-N-demethyl-6-deoxy-6,9-epoxy-6-[(S)-2-azidopropyl]-7,8-nor-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)erythromycin A cyclic 11,12-carbonate (488794-85-0) → 8-epi-(S)-8a-aza-3'-N-demethyl-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)-8a-homoerythromycin A cyclic 11,12-carbonate (488794-88-3)

Guidance literature:

3'-N-demethyl-6-deoxy-6,9-epoxy-6-[(S)-2-azidopropyl]-7,8-nor-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)erythromycin A cyclic 11,12-carbonate; With triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 1h;

With water; In tetrahydrofuran; at 60 ℃; for 3h; Further stages.;

DOI:10.1021/jo020458e

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → 8-epi-(S)-8a-aza-3'-N-demethyl-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)-8a-homoerythromycin A cyclic 11,12-carbonate (488794-88-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 100 percent / NaHCO₃ / dioxane / 1 h / 70 - 75 °C

2.1: K₂CO₃ / tetrahydrofuran / 2 h / 20 °C

3.1: 48.7 g / NaH / tetrahydrofuran; various solvent(s) / 1 h / 20 °C

4.1: 42 percent / pyridinium chlorochromate; Celite / 1,2-dichloro-ethane / 8 h / 50 - 55 °C

5.1: 29 percent / BH₃*THF complex / tetrahydrofuran / 2.08 h

6.1: triethylamine / CH₂Cl₂ / 2 h / -40 - -30 °C

7.1: 1.46 g / water / tetrahydrofuran / 2.5 h / 75 °C

8.1: 87 percent / triphenylphosphine; hydrogen azide; diethyl azodicarboxylate / tetrahydrofuran / 0.67 h

9.1: triphenylphosphine / tetrahydrofuran / 1 h / 20 °C

9.2: 52 percent / water / tetrahydrofuran / 3 h / 60 °C

With borane-THF; hydrogen azide; Celite; water; sodium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; 1,2-dichloro-ethane; 8.1: Mitsunobu reaction / 9.1: Staudinger reduction;

DOI:10.1021/jo020458e

Reference yield:

14-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-8-ethyl-12-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-2,7,11,13,15,17-hexamethyl-4,6,9,18-tetraoxa-tricyclo[13.2.1.03,7]octadec-1(17)-ene-5,10-dione → 8-epi-(S)-8a-aza-3'-N-demethyl-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)-8a-homoerythromycin A cyclic 11,12-carbonate (488794-88-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 100 percent / NaHCO₃ / dioxane / 1 h / 70 - 75 °C

2.1: K₂CO₃ / tetrahydrofuran / 2 h / 20 °C

3.1: 48.7 g / NaH / tetrahydrofuran; various solvent(s) / 1 h / 20 °C

4.1: 42 percent / pyridinium chlorochromate; Celite / 1,2-dichloro-ethane / 8 h / 50 - 55 °C

5.1: 29 percent / BH₃*THF complex / tetrahydrofuran / 2.08 h

6.1: triethylamine / CH₂Cl₂ / 2 h / -40 - -30 °C

7.1: 1.46 g / water / tetrahydrofuran / 2.5 h / 75 °C

8.1: 87 percent / triphenylphosphine; hydrogen azide; diethyl azodicarboxylate / tetrahydrofuran / 0.67 h

9.1: triphenylphosphine / tetrahydrofuran / 1 h / 20 °C

9.2: 52 percent / water / tetrahydrofuran / 3 h / 60 °C

With borane-THF; hydrogen azide; Celite; water; sodium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; 1,2-dichloro-ethane; 8.1: Mitsunobu reaction / 9.1: Staudinger reduction;

DOI:10.1021/jo020458e

upstream raw materials:

3'-N-demethyl-6-deoxy-6,9-epoxy-6-[(S)-2-azidopropyl]-7,8-nor-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)erythromycin A cyclic 11,12-carbonate

benzyl chloroformate

3'-N-demethyl-6-deoxy-6,9-epoxy-7,8-nor-6-(2-oxopropyl)-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)erythromycin A cyclic 11,12-carbonate

3'-N-demethyl-6-deoxy-6,9-epoxy-6-[(S)-2-hydroxypropyl]-7,8-nor-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)erythromycin A cyclic 11,12-carbonate

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