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

Base Information

• Chemical Name: (4R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-<2-<(4S,5R)-5-methoxymethoxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbonyl>-3-methoxyphenyl>acetylpyrrolidine
• CAS No.: 152500-44-2
• Molecular Formula: C₃₅H₄₇NO₁₀
• Molecular Weight: 641.759

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

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

There total 7 articles about (4R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-<2-<(4S,5R)-5-methoxymethoxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbonyl>-3-methoxyphenyl>acetylpyrrolidine 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: 68.0%

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

Guidance literature:

Jones oxidation;

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

Reference yield:

2-bromo-3-methylanisole (38197-43-2) → (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)

Guidance literature:

Multi-step reaction with 6 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

With pyridine; chromium(VI) oxide; 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; acetone;

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

Reference yield:

4-O-benzyl-2,3-O-isopropylidene-D-threose (81801-09-4) → (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)

Guidance literature:

Multi-step reaction with 6 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

With pyridine; chromium(VI) oxide; 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; acetone;

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

upstream raw materials:

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

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

Downstream raw materials:

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

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

(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

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