(3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-5-(R)-thiiranyl-tetrahydro-furo[2,3-d][1,3]dioxole

Base Information

• Chemical Name: (3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-5-(R)-thiiranyl-tetrahydro-furo[2,3-d][1,3]dioxole
• CAS No.: 163592-77-6
• Molecular Formula: C₁₆H₂₀O₄S
• Molecular Weight: 308.398
• Mol file: 163592-77-6.mol

Synonyms:(3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-5-(R)-thiiranyl-tetrahydro-furo[2,3-d][1,3]dioxole

Chemical Property of (3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-5-(R)-thiiranyl-tetrahydro-furo[2,3-d][1,3]dioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-5-(R)-thiiranyl-tetrahydro-furo[2,3-d][1,3]dioxole

There total 4 articles about (3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-5-(R)-thiiranyl-tetrahydro-furo[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: 86.0%

6-S-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-sulfo-6-thio-α-D-glucofuranose potassium salt → (3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-5-(R)-thiiranyl-tetrahydro-furo[2,3-d][1,3]dioxole (163592-77-6)

Guidance literature:

With sodium methylate; In methanol; Ambient temperature;

DOI:10.1021/jo962066b

Reference yield:

3-O-benzyl 1,2-O-isopropylidene-5,6-O-sulfuryl-α-D-glucofuranose (158946-12-4) → (3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-5-(R)-thiiranyl-tetrahydro-furo[2,3-d][1,3]dioxole (163592-77-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / acetone / Ambient temperature

2: 86 percent / NaOMe / methanol / Ambient temperature

With sodium methylate; In methanol; acetone;

DOI:10.1021/jo962066b

Reference yield:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → (3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-5-(R)-thiiranyl-tetrahydro-furo[2,3-d][1,3]dioxole (163592-77-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / SOCl₂, Et₃N / CH₂Cl₂ / 0 °C

2: 83 percent / NaIO₄, RuCl₃*3H₂O / acetonitrile; CCl₄; H₂O / Ambient temperature

3: 100 percent / acetone / Ambient temperature

4: 86 percent / NaOMe / methanol / Ambient temperature

With ruthenium trichloride; sodium periodate; thionyl chloride; sodium methylate; triethylamine; In methanol; tetrachloromethane; dichloromethane; water; acetone; acetonitrile;

DOI:10.1021/jo962066b

upstream raw materials:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

3-O-benzyl 1,2-O-isopropylidene-5,6-O-sulfuryl-α-D-glucofuranose

(3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-yl)-tetrahydro-furo[2,3-d][1,3]dioxole

Downstream raw materials:

6-O-acetyl-5-S-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-thio-β-L-idofuranose

3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-thio-β-L-idofuranose

5-S-acetyl-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-thio-β-L-idofuranose