(3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyl-5-(pent-4-enyl)tetrahydrofuro[2,3-d][1,3]dioxole

Base Information

• Chemical Name: (3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyl-5-(pent-4-enyl)tetrahydrofuro[2,3-d][1,3]dioxole
• CAS No.: 163185-16-8
• Molecular Formula: C₁₉H₂₆O₄
• Molecular Weight: 318.413
• Mol file: 163185-16-8.mol

Synonyms:(3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyl-5-(pent-4-enyl)tetrahydrofuro[2,3-d][1,3]dioxole

Chemical Property of (3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyl-5-(pent-4-enyl)tetrahydrofuro[2,3-d][1,3]dioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyl-5-(pent-4-enyl)tetrahydrofuro[2,3-d][1,3]dioxole

There total 6 articles about (3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyl-5-(pent-4-enyl)tetrahydrofuro[2,3-d][1,3]dioxole 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: 80.0%

4-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-butyraldehyde (163185-27-1) + Methylenetriphenylphosphorane (19493-09-5) → (3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyl-5-(pent-4-enyl)tetrahydrofuro[2,3-d][1,3]dioxole (163185-16-8)

Guidance literature:

In tetrahydrofuran; hexane; toluene;

DOI:10.1021/jo00105a012

Reference yield: 75.0%

O-(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-enyl O-phenyl carbonothioate (1110659-18-1) → (3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyl-5-(pent-4-enyl)tetrahydrofuro[2,3-d][1,3]dioxole (163185-16-8)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 5h; Heating;

DOI:10.1016/j.tetlet.2008.07.057

Reference yield:

benzyl bromide (100-39-0) → (3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyl-5-(pent-4-enyl)tetrahydrofuro[2,3-d][1,3]dioxole (163185-16-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / NaH, n-Bu₄NI / dimethylformamide / 1.) 0 deg C, 15 min, 2.) r.t., 1 h

2: 1.) 9-BBN, 2.) 30percent H₂O₂, 3 N NaOH / 1.) THF, r.t., 8 h, 2.) 0 deg C, 0.5 h

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 25 min, 2.) -78 to 0 deg C

4: 80 percent / tetrahydrofuran; toluene; hexane

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00105a012

upstream raw materials:

4-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-butyraldehyde

Methylenetriphenylphosphorane

benzyl bromide

5,6,7,8-tetradeoxy-1,2-O-isopropylidene-α-D-xylo-oct-7-enofuranose

Downstream raw materials:

(2S,3R,4R)-4-(benzyloxy)-2-methoxy-5-(pent-4-enyl)tetrahydrofuran-3-ol