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

Base Information

• Chemical Name: ((3aS,5S,6S,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanethiol
• CAS No.: 1607447-52-8
• Molecular Formula: C₁₅H₂₀O₄S
• Molecular Weight: 296.387
• Mol file: 1607447-52-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about ((3aS,5S,6S,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanethiol 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: 86.0%

S-(((3aS,5S,6S,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl) ethanethioate (1607447-51-7) → ((3aS,5S,6S,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanethiol (1607447-52-8) + C30H38O8S2

Guidance literature:

With methanol; sodium; for 1h;

DOI:10.1016/j.carres.2014.01.004

Reference yield:

(3aS,5S,6S,6aS)-6-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole (1607447-50-6) → ((3aS,5S,6S,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanethiol (1607447-52-8) + C30H38O8S2

Guidance literature:

Multi-step reaction with 2 steps

1: N,N-dimethyl-formamide / 1 h / 80 °C

2: sodium; methanol / 1 h

With methanol; sodium; In N,N-dimethyl-formamide;

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)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanethiol (1607447-52-8) + C30H38O8S2

Guidance literature:

Multi-step reaction with 7 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

6: N,N-dimethyl-formamide / 1 h / 80 °C

7: sodium; methanol / 1 h

With pyridine; 1H-imidazole; methanol; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; iodine; sodium; sodium hydride; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 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

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

Downstream raw materials:

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