2,2-dimethyl-propionic acid 2-[2-(3-benzyloxy-2-bromo-4-methoxy-benzyl)-4-oxo-3,4-dihydro-2H-pyridin-1-yl]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: 2,2-dimethyl-propionic acid 2-[2-(3-benzyloxy-2-bromo-4-methoxy-benzyl)-4-oxo-3,4-dihydro-2H-pyridin-1-yl]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester
• CAS No.: 891833-58-2
• Molecular Formula: C₄₆H₆₂BrNO₁₂
• Molecular Weight: 900.902

Synonyms:2,2-dimethyl-propionic acid 2-[2-(3-benzyloxy-2-bromo-4-methoxy-benzyl)-4-oxo-3,4-dihydro-2H-pyridin-1-yl]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester

Chemical Property of 2,2-dimethyl-propionic acid 2-[2-(3-benzyloxy-2-bromo-4-methoxy-benzyl)-4-oxo-3,4-dihydro-2H-pyridin-1-yl]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester

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Technology Process of 2,2-dimethyl-propionic acid 2-[2-(3-benzyloxy-2-bromo-4-methoxy-benzyl)-4-oxo-3,4-dihydro-2H-pyridin-1-yl]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester

There total 1 articles about 2,2-dimethyl-propionic acid 2-[2-(3-benzyloxy-2-bromo-4-methoxy-benzyl)-4-oxo-3,4-dihydro-2H-pyridin-1-yl]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl 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:

2,2-dimethyl-propionic acid 2-[2-(3-benzyloxy-2-bromo-4-methoxy-phenyl)-ethylideneamino]-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester + danishefsky's diene (54125-02-9) → 2,2-dimethyl-propionic acid 2-[2-(3-benzyloxy-2-bromo-4-methoxy-benzyl)-4-oxo-3,4-dihydro-2H-pyridin-1-yl]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester + 2,2-dimethyl-propionic acid 2-[2-(3-benzyloxy-2-bromo-4-methoxy-benzyl)-4-oxo-3,4-dihydro-2H-pyridin-1-yl]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester (891833-58-2)

Guidance literature:

2,2-dimethyl-propionic acid 2-[2-(3-benzyloxy-2-bromo-4-methoxy-phenyl)-ethylideneamino]-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester; danishefsky's diene; With zinc(II) chloride; In tetrahydrofuran; at -78 - -20 ℃; for 24h;

With hydrogenchloride;

DOI:10.1002/anie.200504090

Reference yield:

2,2-dimethyl-propionic acid 2-[2-(3-benzyloxy-2-bromo-4-methoxy-benzyl)-4-oxo-3,4-dihydro-2H-pyridin-1-yl]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester (891833-58-2) + N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) → 2,2-dimethyl-propionic acid 2-[2-(3-benzyloxy-2-bromo-4-methoxy-benzyl)-4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridin-1-yl]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 - 20 ℃; for 2h;

DOI:10.1002/anie.200504090

Reference yield:

2,2-dimethyl-propionic acid 2-[2-(3-benzyloxy-2-bromo-4-methoxy-benzyl)-4-oxo-3,4-dihydro-2H-pyridin-1-yl]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester (891833-58-2) → 2,2-dimethyl-propionic acid 2-(7-benzyloxy-8-methoxy-6-pyridin-3-yl-1,2-dihydro-6H-2,6-methano-benzo[d]azocin-3-yl)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester

Guidance literature:

Multi-step reaction with 2 steps

1: L-Selectride / tetrahydrofuran / 2 h / -78 - 20 °C

2: 32 percent / [Pd(PPh₃)2Cl₂]; Cs₂CO₃; H₂O / dimethylformamide / 0.67 h / 80 - 100 °C / microwave irradiation

With bis-triphenylphosphine-palladium(II) chloride; water; L-Selectride; caesium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide; 2: domino Suzuki-Heck coupling;

DOI:10.1002/anie.200504090

upstream raw materials:

danishefsky's diene

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