(3R,4S,5S)-3-(benzyloxymethyl)-1,6-dien-4,5-(O-isopropylidenedioxy)-heptan-3-ol

Base Information

• Chemical Name: (3R,4S,5S)-3-(benzyloxymethyl)-1,6-dien-4,5-(O-isopropylidenedioxy)-heptan-3-ol
• CAS No.: 1067238-45-2
• Molecular Formula: C₁₈H₂₄O₄
• Molecular Weight: 304.386
• Mol file: 1067238-45-2.mol

Synonyms:(3R,4S,5S)-3-(benzyloxymethyl)-1,6-dien-4,5-(O-isopropylidenedioxy)-heptan-3-ol

Chemical Property of (3R,4S,5S)-3-(benzyloxymethyl)-1,6-dien-4,5-(O-isopropylidenedioxy)-heptan-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5S)-3-(benzyloxymethyl)-1,6-dien-4,5-(O-isopropylidenedioxy)-heptan-3-ol

There total 7 articles about (3R,4S,5S)-3-(benzyloxymethyl)-1,6-dien-4,5-(O-isopropylidenedioxy)-heptan-3-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: 76.0%

(2R,3S,4S)-3,4-(O-isopropylidenedioxy)-2-vinyl-hexan-5-en-1,2-diol (1067238-44-1) + di(n-butyl)tin oxide (818-08-6) → (3R,4S,5S)-3-(benzyloxymethyl)-1,6-dien-4,5-(O-isopropylidenedioxy)-heptan-3-ol (1067238-45-2)

Guidance literature:

In toluene; for 3h; Inert atmosphere; Reflux;

DOI:10.1021/jm3004009

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) → (3R,4S,5S)-3-(benzyloxymethyl)-1,6-dien-4,5-(O-isopropylidenedioxy)-heptan-3-ol (1067238-45-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1H-imidazole

2.1: potassium tert-butylate / tetrahydrofuran

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

3.2: 20 °C

4.1: tetrahydrofuran / -78 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

6.1: toluene / 3 h / Inert atmosphere; Reflux

With 1H-imidazole; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; toluene; 2.1: Wittig reaction / 3.1: Swern oxidation / 3.2: Swern oxidation;

DOI:10.1021/jm3004009

Reference yield:

D-Ribose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → (3R,4S,5S)-3-(benzyloxymethyl)-1,6-dien-4,5-(O-isopropylidenedioxy)-heptan-3-ol (1067238-45-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sulfuric acid

2.1: 1H-imidazole

3.1: potassium tert-butylate / tetrahydrofuran

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

4.2: 20 °C

5.1: tetrahydrofuran / -78 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

7.1: toluene / 3 h / Inert atmosphere; Reflux

With 1H-imidazole; oxalyl dichloride; sulfuric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; toluene; 3.1: Wittig reaction / 4.1: Swern oxidation / 4.2: Swern oxidation;

DOI:10.1021/jm3004009

upstream raw materials:

(2R,3S,4S)-3,4-(O-isopropylidenedioxy)-2-vinyl-hexan-5-en-1,2-diol

di(n-butyl)tin oxide

2,3-O-isopropylidene-D-ribofuranose

D-Ribose

Downstream raw materials:

(3aR,4R,6aR)-(6-benzyloxymethyl-5-fluoro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yloxy)-tert-butyl-diphenyl-silane

RX-3117

(4R,5R)3-[(benzoyloxy)methyl]-4,5-O-isopropylidene-2-cyclopentenone

C₂₉H₄₁FN₂O₇SSi₂