1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-(benzyloxymethyl)-2-propen-1-ol

Base Information

• Chemical Name: 1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-(benzyloxymethyl)-2-propen-1-ol
• CAS No.: 681853-97-4
• Molecular Formula: C₁₈H₂₄O₄
• Molecular Weight: 304.386
• Mol file: 681853-97-4.mol

Synonyms:1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-(benzyloxymethyl)-2-propen-1-ol

Chemical Property of 1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-(benzyloxymethyl)-2-propen-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-(benzyloxymethyl)-2-propen-1-ol

There total 6 articles about 1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-(benzyloxymethyl)-2-propen-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: 95.0%

vinyl magnesium bromide (1826-67-1) + (+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-one (681853-94-1) → 1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-(benzyloxymethyl)-2-propen-1-ol (681853-97-4)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1021/jo0356762

Reference yield:

(1R)-(+)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-ol (97204-83-6) → 1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-(benzyloxymethyl)-2-propen-1-ol (681853-97-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / oxalyl chloride; triethylamine; DMSO / CH₂Cl₂ / -78 - 20 °C

2: 95 percent / tetrahydrofuran / -78 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 2: Grignard reaction;

DOI:10.1081/NCN-200061832

Reference yield:

2,3-O-isopropylidene-D-ribofuranose (67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1) → 1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-(benzyloxymethyl)-2-propen-1-ol (681853-97-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium tert-butoxide / tetrahydrofuran / 1.33 h / 0 - 20 °C

1.2: tetrahydrofuran / 12 h / 20 °C

2.1: dibutyltin oxide / toluene / 3 h / Heating

2.2: 80 percent / tetrabutylammonium iodide / toluene / 16 h / 75 °C

3.1: 92 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1 h / 20 °C

4.1: 95 percent / tetrahydrofuran / 1 h / -78 °C

With oxalyl dichloride; potassium tert-butylate; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; toluene; 1.2: Wittig reaction / 3.1: Swern oxidation / 4.1: Grignard reaction;

DOI:10.1021/jo0356762

upstream raw materials:

vinyl magnesium bromide

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

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

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

Downstream raw materials:

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

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

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