(1R)-(+)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-ol

Base Information

• Chemical Name: (1R)-(+)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-ol
• CAS No.: 97204-83-6
• Molecular Formula: C₁₆H₂₂O₄
• Molecular Weight: 278.348
• Mol file: 97204-83-6.mol

Synonyms:(1R)-(+)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-ol

Chemical Property of (1R)-(+)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-(+)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-ol

There total 11 articles about (1R)-(+)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-ol 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%

benzyl bromide (100-39-0) + (1R)-1-((4R,5S)-2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)ethane-1,2-diol (116780-31-5) → (1R)-(+)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-ol (97204-83-6)

Guidance literature:

(1R)-1-((4R,5S)-2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)ethane-1,2-diol; With di(n-butyl)tin oxide; In toluene; for 3h; Heating;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In toluene; at 75 ℃; for 16h;

DOI:10.1021/jo0356762

Reference yield: 80.0%

5-O-benzyl-2,3-O-isopropylidene-D-ribofuranose (198969-39-0) + Methyltriphenylphosphonium bromide (1779-49-3) → (1R)-(+)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-ol (97204-83-6)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 20 ℃;

DOI:10.1081/NCN-200061832

Reference yield: 80.0%

2,3-O-isopropylidene-D-ribofuranose (67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1) + Methyltriphenylphosphonium bromide (1779-49-3) + benzyl bromide (100-39-0) → (1R)-(+)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-ol (97204-83-6)

Guidance literature:

2,3-O-isopropylidene-D-ribofuranose; Methyltriphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 12h;

With di(n-butyl)tin oxide; In toluene; Heating;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; at 75 ℃; for 16h;

DOI:10.1246/cl.2004.506

upstream raw materials:

5-O-benzyl-2,3-O-isopropylidene-D-ribofuranose

Methyltriphenylphosphonium bromide

Methylenetriphenylphosphorane

benzyl bromide

Downstream raw materials:

(+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-one

(3aS,4S,6aS)-4-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

(3aR,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-one

(1R,4S,5S)-1-(benzyloxymethyl)-2-en-4,5-(O-isopropylidenedioxy)-cyclopentan-1-ol