3-<(2R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonylpyrrolidin-2-yl>-1-<(4R,5R)-5-methoxymethoxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl>-8-methoxyisoquinoline

Base Information

• Chemical Name: 3-<(2R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonylpyrrolidin-2-yl>-1-<(4R,5R)-5-methoxymethoxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl>-8-methoxyisoquinoline
• CAS No.: 152500-46-4
• Molecular Formula: C₃₅H₄₆N₂O₈
• Molecular Weight: 622.759

Synonyms:3-<(2R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonylpyrrolidin-2-yl>-1-<(4R,5R)-5-methoxymethoxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl>-8-methoxyisoquinoline

Chemical Property of 3-<(2R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonylpyrrolidin-2-yl>-1-<(4R,5R)-5-methoxymethoxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl>-8-methoxyisoquinoline

Chemical Property:

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Technology Process of 3-<(2R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonylpyrrolidin-2-yl>-1-<(4R,5R)-5-methoxymethoxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl>-8-methoxyisoquinoline

There total 8 articles about 3-<(2R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonylpyrrolidin-2-yl>-1-<(4R,5R)-5-methoxymethoxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl>-8-methoxyisoquinoline 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: 72.0%

(4R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-<2-<(4S,5R)-5-methoxymethoxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbonyl>-3-methoxyphenyl>acetylpyrrolidine (152500-44-2) → 3-<(2R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonylpyrrolidin-2-yl>-1-<(4R,5R)-5-methoxymethoxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl>-8-methoxyisoquinoline (152500-46-4)

Guidance literature:

With ammonium hydroxide; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0040-4039(00)73850-0

Reference yield:

2-bromo-3-methylanisole (38197-43-2) → 3-<(2R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonylpyrrolidin-2-yl>-1-<(4R,5R)-5-methoxymethoxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl>-8-methoxyisoquinoline (152500-46-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / n-butyllihium / hexane; diethyl ether / 0.75 h / -78 °C

2: 98 percent / pyridine, chromium (VI) oxide / CH₂Cl₂ / 0.75 h / Ambient temperature

3: 98 percent / hydrogen / 20percent Pd/C / methanol / 15 h / 760 Torr / Ambient temperature

4: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 17 h / Ambient temperature

5: 48 percent / lithium diisopropylamide, N,N,N',N'-tetramethylethylenediamine / tetrahydrofuran; hexane / 2 h / -78 °C

6: 68 percent / 2.6 M Jones reagent, celite / acetone / 0.33 h / Ambient temperature

7: 72 percent / 38percent ammonia / H₂O; tetrahydrofuran / 15 h / Ambient temperature

With pyridine; chromium(VI) oxide; ammonium hydroxide; n-butyllithium; jones reagent; N,N,N,N,-tetramethylethylenediamine; Celite; hydrogen; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone;

DOI:10.1016/S0040-4020(01)80644-X

Reference yield:

4-O-benzyl-2,3-O-isopropylidene-D-threose (81801-09-4) → 3-<(2R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonylpyrrolidin-2-yl>-1-<(4R,5R)-5-methoxymethoxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl>-8-methoxyisoquinoline (152500-46-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / n-butyllihium / hexane; diethyl ether / 0.75 h / -78 °C

2: 98 percent / pyridine, chromium (VI) oxide / CH₂Cl₂ / 0.75 h / Ambient temperature

3: 98 percent / hydrogen / 20percent Pd/C / methanol / 15 h / 760 Torr / Ambient temperature

4: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 17 h / Ambient temperature

5: 48 percent / lithium diisopropylamide, N,N,N',N'-tetramethylethylenediamine / tetrahydrofuran; hexane / 2 h / -78 °C

6: 68 percent / 2.6 M Jones reagent, celite / acetone / 0.33 h / Ambient temperature

7: 72 percent / 38percent ammonia / H₂O; tetrahydrofuran / 15 h / Ambient temperature

With pyridine; chromium(VI) oxide; ammonium hydroxide; n-butyllithium; jones reagent; N,N,N,N,-tetramethylethylenediamine; Celite; hydrogen; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone;

DOI:10.1016/S0040-4020(01)80644-X

upstream raw materials:

(4R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-<2-<(4S,5R)-5-methoxymethoxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbonyl>-3-methoxyphenyl>acetylpyrrolidine

2-bromo-3-methylanisole

4-O-benzyl-2,3-O-isopropylidene-D-threose

2-<(4S,5R)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbonyl>-3-methylanisole

Downstream raw materials:

(2S,5R)-2-Benzyloxymethyl-5-((1R,5S,10bR)-1-hydroxymethyl-10-methoxy-3-oxo-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinolin-5-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

(1R,3S)-3-((2R,5S)-5-Benzyloxymethyl-1-tert-butoxycarbonyl-pyrrolidin-2-yl)-1-formyl-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 2,2,2-trichloro-ethyl ester

(1R,3R)-2,2,2-trichloroethyl 3-<(2R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonylpyrrolidin-2-yl>-1-hydroxymethyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

(1R,3R)-2,2,2-trichloroethyl 1-acetoxymethyl-3-<(2R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonylpyrrolidin-2-yl>-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate

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