8-(R)-3'-N-demethyl-8a-oxa-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)-8a-homoerythromycin A

Base Information

Chemical Name:8-(R)-3'-N-demethyl-8a-oxa-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)-8a-homoerythromycin A
CAS No.:488794-92-9
Molecular Formula:C₆₀H₈₃NO₂₀
Molecular Weight:1138.31
Hs Code.:

Synonyms:8-(R)-3'-N-demethyl-8a-oxa-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)-8a-homoerythromycin A

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Chemical Property of 8-(R)-3'-N-demethyl-8a-oxa-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)-8a-homoerythromycin A

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Technology Process of 8-(R)-3'-N-demethyl-8a-oxa-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)-8a-homoerythromycin A

There total 10 articles about 8-(R)-3'-N-demethyl-8a-oxa-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)-8a-homoerythromycin A 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: 65.0%

: 488794-82-7
8-(R)-3'-N-demethyl-8a-oxa-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)-8a-homoerythromycin A cyclic 11,12-carbonate

: 488794-92-9
8-(R)-3'-N-demethyl-8a-oxa-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)-8a-homoerythromycin A

Guidance literature:: With 1,4-bis(bromomagnesium)butane; In tetrahydrofuran; at -78 ℃; for 2.83333h;
DOI:10.1021/jo020458e

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 488794-92-9
8-(R)-3'-N-demethyl-8a-oxa-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)-8a-homoerythromycin A

Guidance literature:: Multi-step reaction with 9 steps

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

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

3: 48.7 g / NaH / tetrahydrofuran; various solvent(s) / 1 h / 20 °C

4: 42 percent / pyridinium chlorochromate; Celite / 1,2-dichloro-ethane / 8 h / 50 - 55 °C

5: 29 percent / BH₃*THF complex / tetrahydrofuran / 2.08 h

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

7: 1.46 g / water / tetrahydrofuran / 2.5 h / 75 °C

8: 98 percent / NaH / tetrahydrofuran; various solvent(s) / 0.83 h / 20 °C

9: 65 percent / BrMg(CH₂)4MgBr / tetrahydrofuran / 2.83 h / -78 °C

With borane-THF; Celite; water; sodium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; pyridinium chlorochromate; 1,4-bis(bromomagnesium)butane; In tetrahydrofuran; 1,4-dioxane; dichloromethane; 1,2-dichloro-ethane;
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[13.2.1.0^3,7]octadec-1⁽¹⁷⁾-ene-5,10-dione

: 488794-92-9
8-(R)-3'-N-demethyl-8a-oxa-2'-O,3'-N,4''-O-tris(benzyloxycarbonyl)-8a-homoerythromycin A

Guidance literature:: Multi-step reaction with 9 steps

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

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

3: 48.7 g / NaH / tetrahydrofuran; various solvent(s) / 1 h / 20 °C

4: 42 percent / pyridinium chlorochromate; Celite / 1,2-dichloro-ethane / 8 h / 50 - 55 °C

5: 29 percent / BH₃*THF complex / tetrahydrofuran / 2.08 h

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

7: 1.46 g / water / tetrahydrofuran / 2.5 h / 75 °C

8: 98 percent / NaH / tetrahydrofuran; various solvent(s) / 0.83 h / 20 °C

9: 65 percent / BrMg(CH₂)4MgBr / tetrahydrofuran / 2.83 h / -78 °C

With borane-THF; Celite; water; sodium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; pyridinium chlorochromate; 1,4-bis(bromomagnesium)butane; In tetrahydrofuran; 1,4-dioxane; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1021/jo020458e