(4R,5R)-4-benzyloxymethyl-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane

Base Information

• Chemical Name: (4R,5R)-4-benzyloxymethyl-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane
• CAS No.: 860267-59-0
• Molecular Formula: C₁₇H₂₄O₃
• Molecular Weight: 276.376
• Mol file: 860267-59-0.mol

Synonyms:(4R,5R)-4-benzyloxymethyl-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane

Chemical Property of (4R,5R)-4-benzyloxymethyl-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R)-4-benzyloxymethyl-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane

There total 4 articles about (4R,5R)-4-benzyloxymethyl-5-but-3-enyl-2,2-dimethyl-[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: 74.0%

1-O-benzyl-2,3-O-isopropylidene-D-threitol (78469-77-9) + allylmagnesium bromide (1730-25-2) → (4R,5R)-4-benzyloxymethyl-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane (860267-59-0)

Guidance literature:

1-O-benzyl-2,3-O-isopropylidene-D-threitol; With trifluoromethylsulfonic anhydride; triethylamine; In dichloromethane; at -40 ℃; for 1h;

allylmagnesium bromide; With copper(I) bromide; In diethyl ether; for 2.5h;

DOI:10.1016/j.tetasy.2010.01.011

Reference yield:

Trifluoro-methanesulfonic acid (4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (133842-56-5) + allylmagnesium bromide (1730-25-2) → (4R,5R)-4-benzyloxymethyl-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane (860267-59-0)

Guidance literature:

allylmagnesium bromide; With copper(I) bromide; In diethyl ether; at 0 ℃; for 0.25h;

Trifluoro-methanesulfonic acid (4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester; In diethyl ether; at 0 ℃; for 2.5h;

DOI:10.1021/ol0508126

Reference yield:

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol (73346-74-4) → (4R,5R)-4-benzyloxymethyl-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane (860267-59-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 88 percent / NaH / dimethylformamide

2.1: 19.9 g / triethylamine / CH₂Cl₂ / 1 h / -15 °C

3.1: CuBr / diethyl ether / 0.25 h / 0 °C

3.2: 11.2 g / diethyl ether / 2.5 h / 0 °C

With sodium hydride; triethylamine; copper(I) bromide; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol0508126

upstream raw materials:

Trifluoro-methanesulfonic acid (4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

allylmagnesium bromide

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

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

Downstream raw materials:

C₂₀H₃₀O₄

(1'R,2R,3R,6R)-6-(1'-hydroxy-2'-p-toluenesulfonyloxy-ethyl)-3-methoxy-methoxy-2-tetradecyl-tetrahydropyran

(1'R,2R,3R,6R)-6-(1',2'-bis-benzyloxy-ethyl)-2-tetradec-2-enyl-tetrahydro-pyran-3-ol

(E)-3-[(1R,2R)-2,3-Bis-benzyloxy-1-(2-[1,3]dithian-2-yl-ethyl)-propoxy]-acrylic acid ethyl ester