3-O-descladinosyl-3-O-[3-(5-pyrimidyl)-(E)-prop-2-enyl]-6-O-methylerythromycin A 9-(E)-O-(2,4,6-trimethylbenzyl)oxime 11,12-cyclic carbonate

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Chemical Name:3-O-descladinosyl-3-O-[3-(5-pyrimidyl)-(E)-prop-2-enyl]-6-O-methylerythromycin A 9-(E)-O-(2,4,6-trimethylbenzyl)oxime 11,12-cyclic carbonate
CAS No.:1360059-89-7
Molecular Formula:C₄₈H₇₂N₄O₁₁
Molecular Weight:881.12
Hs Code.:

Synonyms:3-O-descladinosyl-3-O-[3-(5-pyrimidyl)-(E)-prop-2-enyl]-6-O-methylerythromycin A 9-(E)-O-(2,4,6-trimethylbenzyl)oxime 11,12-cyclic carbonate

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Chemical Property of 3-O-descladinosyl-3-O-[3-(5-pyrimidyl)-(E)-prop-2-enyl]-6-O-methylerythromycin A 9-(E)-O-(2,4,6-trimethylbenzyl)oxime 11,12-cyclic carbonate

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Technology Process of 3-O-descladinosyl-3-O-[3-(5-pyrimidyl)-(E)-prop-2-enyl]-6-O-methylerythromycin A 9-(E)-O-(2,4,6-trimethylbenzyl)oxime 11,12-cyclic carbonate

There total 8 articles about 3-O-descladinosyl-3-O-[3-(5-pyrimidyl)-(E)-prop-2-enyl]-6-O-methylerythromycin A 9-(E)-O-(2,4,6-trimethylbenzyl)oxime 11,12-cyclic 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: 19.0%

: 4595-59-9
5-bromopyrimidine

: 1360059-88-6
C₄₆H₇₂N₂O₁₂

: 1360059-89-7
3-O-descladinosyl-3-O-[3-(5-pyrimidyl)-(E)-prop-2-enyl]-6-O-methylerythromycin A 9-(E)-O-(2,4,6-trimethylbenzyl)oxime 11,12-cyclic carbonate

Guidance literature:: 5-bromopyrimidine; C₄₆H₇₂N₂O₁₂; With trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); tetrabutylammomium bromide; sodium acetate; In N,N-dimethyl-formamide; at 100 ℃; for 72h; Inert atmosphere;

With methanol; at 65 ℃; for 3h;
DOI:10.1016/j.ejmech.2012.01.023

Reference yield:

: 1360059-82-0
2'-O-acetyl-3-O-descladinosyl-3-O-allyl-6-O-methylerythromycin A 9-(E)-O-acetyl-oxime

: 1360059-89-7
3-O-descladinosyl-3-O-[3-(5-pyrimidyl)-(E)-prop-2-enyl]-6-O-methylerythromycin A 9-(E)-O-(2,4,6-trimethylbenzyl)oxime 11,12-cyclic carbonate

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridine / dichloromethane / 18 h / -5 °C

2.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.25 h / 20 °C

2.2: 1 h / 20 °C

3.1: trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); tetrabutylammomium bromide; sodium acetate / N,N-dimethyl-formamide / 72 h / 100 °C / Inert atmosphere

3.2: 3 h / 65 °C

With pyridine; trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); potassium tert-butylate; tetrabutylammomium bromide; sodium acetate; In dichloromethane; N,N-dimethyl-formamide; 3.1: Heck reaction;
DOI:10.1016/j.ejmech.2012.01.023

Reference yield:

: 791845-56-2
2',4-O-bis(trimethylsilyl)-6-O-methylerythromycin A 9-(E)-O-(1-isopropoxycyclohexyl)-oxime

: 1360059-89-7
3-O-descladinosyl-3-O-[3-(5-pyrimidyl)-(E)-prop-2-enyl]-6-O-methylerythromycin A 9-(E)-O-(2,4,6-trimethylbenzyl)oxime 11,12-cyclic carbonate

Guidance literature:: Multi-step reaction with 8 steps

1.1: hydrogenchloride / ethanol; water / 1 h / 40 °C

1.2: pH 9

2.1: pyridine hydrochloride / acetonitrile / 3 h / 20 °C

2.2: 0.67 h / 0 °C

3.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.12 h / 20 °C

4.1: hydrogenchloride / ethanol; water / 1 h / 30 °C

4.2: pH 9

5.1: dichloromethane / 1 h / 20 °C

6.1: pyridine / dichloromethane / 18 h / -5 °C

7.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.25 h / 20 °C

7.2: 1 h / 20 °C

8.1: trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); tetrabutylammomium bromide; sodium acetate / N,N-dimethyl-formamide / 72 h / 100 °C / Inert atmosphere

8.2: 3 h / 65 °C

With pyridine; hydrogenchloride; trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); potassium tert-butylate; tetrabutylammomium bromide; sodium acetate; pyridine hydrochloride; In ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 8.1: Heck reaction;
DOI:10.1016/j.ejmech.2012.01.023