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

Base Information

• Chemical Name: 1-((4R,5R)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propane-2-one
• CAS No.: 91526-99-7
• Molecular Formula: C₁₆H₂₂O₄
• Molecular Weight: 278.348
• Mol file: 91526-99-7.mol

Synonyms:1-((4R,5R)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propane-2-one

Chemical Property of 1-((4R,5R)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propane-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-((4R,5R)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propane-2-one

There total 17 articles about 1-((4R,5R)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propane-2-one 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: 87.0%

benzyl (4R,5R)-2,2-dimethyl-5-(2-methyl-1,3-dithian-2-ylmethyl)-1,3-dioxolan-4-ylmethyl ether (91526-98-6) → 1-((4R,5R)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propane-2-one (91526-99-7)

Guidance literature:

With calcium carbonate; methyl iodide; In water; acetonitrile; for 10h; Heating;

DOI:10.1021/jo0518093

Reference yield:

1-O-benzyl-2,3-O-isopropylidene-D-threitol (78469-77-9) → 1-((4R,5R)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propane-2-one (91526-99-7)

Guidance literature:

Multi-step reaction with 4 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

With 1H-imidazole; iodine; tert.-butyl lithium; triphenylphosphine; calcium carbonate; methyl iodide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; water; toluene; acetonitrile;

DOI:10.1021/jo0518093

Reference yield:

(4R,5S)-4-((benzyloxy)methyl)-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane (114826-50-5) → 1-((4R,5R)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propane-2-one (91526-99-7)

Guidance literature:

Multi-step reaction with 3 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

With tert.-butyl lithium; calcium carbonate; methyl iodide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; water; acetonitrile;

DOI:10.1021/jo0518093

upstream raw materials:

2-methyl-1,3-dithian

(4S,5R)-5-benzyloxymethyl-4-bromomethyl-2,2-dimethyl-1,3-dioxolane

benzyl (4R,5R)-2,2-dimethyl-5-(2-methyl-1,3-dithian-2-ylmethyl)-1,3-dioxolan-4-ylmethyl ether

(4R,5R)-4-(benzyloxymethyl)-5-(1,3-dithian-2-ylmethyl)-2,2-dimethyl-1,3-dioxolane

Downstream raw materials:

(2S,4R,5R)-6-benzyloxy-4,5-isopropylidenedioxy-2-hexanol

(2R,4R,5R)-6-benzyloxy-4,5-isopropylidenedioxy-2-hexanol

(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