(4S,5R)-2,2-Dimethyl-5-(2-oxo-propyl)-[1,3]dioxolane-4-carboxylic acid (2-benzyloxy-ethyl)-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amide

Base Information

• Chemical Name: (4S,5R)-2,2-Dimethyl-5-(2-oxo-propyl)-[1,3]dioxolane-4-carboxylic acid (2-benzyloxy-ethyl)-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amide
• CAS No.: 872831-88-4
• Molecular Formula: C₂₆H₃₀BrNO₇
• Molecular Weight: 548.431
• Mol file: 872831-88-4.mol

Synonyms:(4S,5R)-2,2-Dimethyl-5-(2-oxo-propyl)-[1,3]dioxolane-4-carboxylic acid (2-benzyloxy-ethyl)-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amide

Chemical Property of (4S,5R)-2,2-Dimethyl-5-(2-oxo-propyl)-[1,3]dioxolane-4-carboxylic acid (2-benzyloxy-ethyl)-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-2,2-Dimethyl-5-(2-oxo-propyl)-[1,3]dioxolane-4-carboxylic acid (2-benzyloxy-ethyl)-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amide

There total 18 articles about (4S,5R)-2,2-Dimethyl-5-(2-oxo-propyl)-[1,3]dioxolane-4-carboxylic acid (2-benzyloxy-ethyl)-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amide 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: 84.0%

(4S,5R)-2,2-dimethyl-5-(2-oxopropyl)-1,3-dioxolane-4-carboxylic acid (872831-90-8) + (2-benzyloxy-ethyl)-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amine (872831-89-5) → (4S,5R)-2,2-Dimethyl-5-(2-oxo-propyl)-[1,3]dioxolane-4-carboxylic acid (2-benzyloxy-ethyl)-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amide (872831-88-4)

Guidance literature:

With 2-fluoro-1-ethylpyridinium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo0518093

Reference yield:

(4R,5S)-4-((benzyloxy)methyl)-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane (114826-50-5) → (4S,5R)-2,2-Dimethyl-5-(2-oxo-propyl)-[1,3]dioxolane-4-carboxylic acid (2-benzyloxy-ethyl)-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amide (872831-88-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / -78 °C

1.2: 46 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2 h / -78 - 20 °C

2.1: t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / -78 °C

2.2: 87 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1.5 h / -78 °C

3.1: 87 percent / CaCO₃; methyl iodide / acetonitrile; H₂O / 10 h / Heating

4.1: 97 percent / H₂ / Pd/C / ethanol

5.1: 80 percent / ruthenium(III) chloride hydrate; NaIO₄ / CCl₄; acetonitrile; H₂O

6.1: 84 percent / iPr₂NEt; 2-fluoro-1-ethylpyridinium tetrafluoroborate / CH₂Cl₂ / 0 - 20 °C

With ruthenium trichloride; sodium periodate; hydrogen; tert.-butyl lithium; 2-fluoro-1-ethylpyridinium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; calcium carbonate; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; hexane; dichloromethane; water; acetonitrile;

DOI:10.1021/jo0518093

Reference yield:

1-O-benzyl-2,3-O-isopropylidene-D-threitol (78469-77-9) → (4S,5R)-2,2-Dimethyl-5-(2-oxo-propyl)-[1,3]dioxolane-4-carboxylic acid (2-benzyloxy-ethyl)-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amide (872831-88-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 98 percent / triphenylphosphine; I₂; imidazole / toluene / 0.33 h / Heating

2.1: t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / -78 °C

2.2: 46 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2 h / -78 - 20 °C

3.1: t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / -78 °C

3.2: 87 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1.5 h / -78 °C

4.1: 87 percent / CaCO₃; methyl iodide / acetonitrile; H₂O / 10 h / Heating

5.1: 97 percent / H₂ / Pd/C / ethanol

6.1: 80 percent / ruthenium(III) chloride hydrate; NaIO₄ / CCl₄; acetonitrile; H₂O

7.1: 84 percent / iPr₂NEt; 2-fluoro-1-ethylpyridinium tetrafluoroborate / CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; ruthenium trichloride; sodium periodate; hydrogen; iodine; tert.-butyl lithium; 2-fluoro-1-ethylpyridinium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; calcium carbonate; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; hexane; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/jo0518093

upstream raw materials:

(4S,5R)-2,2-dimethyl-5-(2-oxopropyl)-1,3-dioxolane-4-carboxylic acid

(2-benzyloxy-ethyl)-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amine

1-((4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propane-2-one

((4S,5R)-5-(((tert-butyl-dimethyl)silyl-oxy)-methyl)-2,2-dimethyl 1,3-dioxolan-4-yl) methanyl iodide