(3aS,5S,6S,6aS)-6-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Base Information

• Chemical Name: (3aS,5S,6S,6aS)-6-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole
• CAS No.: 1607447-50-6
• Molecular Formula: C₁₅H₁₉IO₄
• Molecular Weight: 390.218
• Mol file: 1607447-50-6.mol

Synonyms:(3aS,5S,6S,6aS)-6-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Chemical Property of (3aS,5S,6S,6aS)-6-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,5S,6S,6aS)-6-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

There total 5 articles about (3aS,5S,6S,6aS)-6-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[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: 94.0%

((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (19139-80-1,34370-91-7,68354-70-1,70798-12-8,59358-33-7) → (3aS,5S,6S,6aS)-6-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole (1607447-50-6)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In toluene; at 100 ℃; for 1h;

DOI:10.1016/j.carres.2014.01.004

Reference yield:

(((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methoxy)(tert-butyl)diphenylsilane (168103-00-2) → (3aS,5S,6S,6aS)-6-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole (1607447-50-6)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h

2: 1H-imidazole; iodine; triphenylphosphine / toluene / 1 h / 100 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; iodine; triphenylphosphine; In tetrahydrofuran; toluene;

DOI:10.1016/j.carres.2014.01.004

Reference yield:

D-arabinofuranose (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) → (3aS,5S,6S,6aS)-6-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole (1607447-50-6)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / 0 - 4 °C / Inert atmosphere

2: camphor-10-sulfonic acid / dichloromethane / 4 °C / Inert atmosphere

3: sodium hydride / 3 h / 20 °C

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h

5: 1H-imidazole; iodine; triphenylphosphine / toluene / 1 h / 100 °C

With pyridine; 1H-imidazole; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; iodine; sodium hydride; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/j.carres.2014.01.004

upstream raw materials:

(3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

(((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methoxy)(tert-butyl)diphenylsilane

((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

D-arabinofuranose

Downstream raw materials:

((3aS,5S,6S,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanethiol

sodium ((3aS,5S,6S,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanesulphonate

S-(((3aS,5S,6S,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl) ethanethioate