(4R,5R)-4-((benzyloxy)methyl)-2,2-dimethyl-5-vinyl-1,3-dioxolane

Base Information

• Chemical Name: (4R,5R)-4-((benzyloxy)methyl)-2,2-dimethyl-5-vinyl-1,3-dioxolane
• CAS No.: 1456722-23-8
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• Mol file: 1456722-23-8.mol

Synonyms:(4R,5R)-4-((benzyloxy)methyl)-2,2-dimethyl-5-vinyl-1,3-dioxolane

Chemical Property of (4R,5R)-4-((benzyloxy)methyl)-2,2-dimethyl-5-vinyl-1,3-dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R)-4-((benzyloxy)methyl)-2,2-dimethyl-5-vinyl-1,3-dioxolane

There total 2 articles about (4R,5R)-4-((benzyloxy)methyl)-2,2-dimethyl-5-vinyl-1,3-dioxolane 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:

Methyltriphenylphosphonium bromide (1779-49-3) + 4-O-benzyl-2,3-O-isopropylidene-D-threose (81801-09-4) → (4R,5R)-4-((benzyloxy)methyl)-2,2-dimethyl-5-vinyl-1,3-dioxolane (1456722-23-8)

Guidance literature:

Methyltriphenylphosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at -10 - 20 ℃; for 1h; Inert atmosphere;

4-O-benzyl-2,3-O-isopropylidene-D-threose; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.08.020

Reference yield:

1-O-benzyl-2,3-O-isopropylidene-D-threitol (78469-77-9) → (4R,5R)-4-((benzyloxy)methyl)-2,2-dimethyl-5-vinyl-1,3-dioxolane (1456722-23-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / tetrahydrofuran; dimethyl sulfoxide / 2 h / 20 °C / Inert atmosphere

2.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -10 - 20 °C / Inert atmosphere

2.2: 2 h / 20 °C / Inert atmosphere

With sodium hexamethyldisilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1016/j.tetlet.2013.08.020

Reference yield:

(4R,5R)-4-((benzyloxy)methyl)-2,2-dimethyl-5-vinyl-1,3-dioxolane (1456722-23-8) → (R)-1-(((1-bromopent-1-yn-3-yl)oxy)methyl)-4-methoxybenzene (1456722-17-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 1 h / 20 °C / Inert atmosphere

2.1: 1H-imidazole; triphenylphosphine; iodine / benzene / 1.5 h / 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 3 h / -78 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

4.2: 30 h / 20 °C

5.1: ozone / dichloromethane / 0.08 h / -78 °C / Inert atmosphere

5.2: Inert atmosphere

6.1: potassium carbonate / methanol / 14 h / 0 - 20 °C / Inert atmosphere

7.1: N-Bromosuccinimide; silver nitrate / acetone / 1 h / 0 °C / Inert atmosphere

With 1H-imidazole; N-Bromosuccinimide; n-butyllithium; hydrogen; iodine; palladium(II) hydroxide; sodium hydride; potassium carbonate; ozone; silver nitrate; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; acetone; benzene;

DOI:10.1016/j.tetlet.2013.08.020

upstream raw materials:

Methyltriphenylphosphonium bromide

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

1-O-benzyl-2,3-O-isopropylidene-D-threitol

Downstream raw materials:

(R)-1-methoxy-4-((pent-1-en-3-yloxy)methyl)benzene

(R)-1-methoxy-4-((pent-1-yn-3-yloxy)methyl)benzene

(3R)-3-[(4-methoxybenzyl)oxy]pentanal

(R)-1-(((1-bromopent-1-yn-3-yl)oxy)methyl)-4-methoxybenzene