2'-O-Acetyl-11-deoxy-11-(carboxyamino)-4''-O-(benzyloxycarbonyl)-6-O-methylerythromycin A 11,12-(cyclic ester)

Base Information

Chemical Name:2'-O-Acetyl-11-deoxy-11-(carboxyamino)-4''-O-(benzyloxycarbonyl)-6-O-methylerythromycin A 11,12-(cyclic ester)
CAS No.:113830-15-2
Molecular Formula:C₄₉H₇₆N₂O₁₆
Molecular Weight:949.146
Hs Code.:

Synonyms:2'-O-Acetyl-11-deoxy-11-(carboxyamino)-4''-O-(benzyloxycarbonyl)-6-O-methylerythromycin A 11,12-(cyclic ester)

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Chemical Property of 2'-O-Acetyl-11-deoxy-11-(carboxyamino)-4''-O-(benzyloxycarbonyl)-6-O-methylerythromycin A 11,12-(cyclic ester)

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Technology Process of 2'-O-Acetyl-11-deoxy-11-(carboxyamino)-4''-O-(benzyloxycarbonyl)-6-O-methylerythromycin A 11,12-(cyclic ester)

There total 7 articles about 2'-O-Acetyl-11-deoxy-11-(carboxyamino)-4''-O-(benzyloxycarbonyl)-6-O-methylerythromycin A 11,12-(cyclic ester) 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: 64.0%

: 113777-95-0
C₄₉H₇₆N₂O₁₆

: 113830-15-2
2'-O-Acetyl-11-deoxy-11-(carboxyamino)-4''-O-(benzyloxycarbonyl)-6-O-methylerythromycin A 11,12-(cyclic ester)

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; at 0 - 5 ℃; for 0.5h;
DOI:10.1021/jo00245a038

Reference yield: 6.0%

: 1189-71-5
isocyanate de chlorosulfonyle

: 113777-92-7
2'-O-acetyl-4''-O-(benzyloxycarbonyl)-10,11-didehydro-6-O-methylerythromycin A

: 113777-93-8
C₄₉H₇₆N₂O₁₆

: 113830-15-2
2'-O-Acetyl-11-deoxy-11-(carboxyamino)-4''-O-(benzyloxycarbonyl)-6-O-methylerythromycin A 11,12-(cyclic ester)

Guidance literature:: In dichloromethane; at 0 - 25 ℃; for 5.5h;
DOI:10.1021/jo00245a038

Reference yield:

: 81103-11-9
clarithromycin

: 113830-15-2
2'-O-Acetyl-11-deoxy-11-(carboxyamino)-4''-O-(benzyloxycarbonyl)-6-O-methylerythromycin A 11,12-(cyclic ester)

Guidance literature:: Multi-step reaction with 5 steps

1: 73 percent / triethylamine / CH₂Cl₂ / 5.5 h

2: 87 percent / (dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 1.) -40 deg C, 1 h, 2.) -20 deg C, 72 h

3: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -35 deg C, 10 min, 2.) RT, 15 min

4: 94 percent / DBU / benzene / 22 h / Heating

5: 6 percent / CH₂Cl₂ / 5.5 h / 0 - 25 °C

With dmap; sodium hexamethyldisilazane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; benzene;
DOI:10.1021/jo00245a038