(3S,5S,7R)-5-fluoro-2,2-dimethyl-3,4,5,7-tetrahydro-1,3-benzodioxole

Base Information

• Chemical Name: (3S,5S,7R)-5-fluoro-2,2-dimethyl-3,4,5,7-tetrahydro-1,3-benzodioxole
• CAS No.: 927682-02-8
• Molecular Formula: C₉H₁₃FO₂
• Molecular Weight: 172.199
• Mol file: 927682-02-8.mol

Synonyms:

Chemical Property of (3S,5S,7R)-5-fluoro-2,2-dimethyl-3,4,5,7-tetrahydro-1,3-benzodioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5S,7R)-5-fluoro-2,2-dimethyl-3,4,5,7-tetrahydro-1,3-benzodioxole

There total 5 articles about (3S,5S,7R)-5-fluoro-2,2-dimethyl-3,4,5,7-tetrahydro-1,3-benzodioxole 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:

tert-butyl(2,2-dimethyl-3S,4S,7S-tetrahydro-1,3-benzodioxol-4-yl)dimethylsilane (256942-69-5) → (3S,5S,7R)-5-fluoro-2,2-dimethyl-3,4,5,7-tetrahydro-1,3-benzodioxole (927682-02-8) + (3S,5R,7R)-5-fluoro-2,2-dimethyl-3,4,5,7-tetrahydro-1,3-benzodioxole (927682-01-7)

Guidance literature:

With sodium hydrogencarbonate; Selectfluor; In acetonitrile; at 20 ℃; for 72h;

Reference yield:

cyclohexa-1,4-diene (1165952-92-0) → (3S,5S,7R)-5-fluoro-2,2-dimethyl-3,4,5,7-tetrahydro-1,3-benzodioxole (927682-02-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: s-BuLi; tetramethylethylenediamine / tetrahydrofuran / -78 - -45 °C

1.2: 75 percent / tetrahydrofuran / 1 h / 20 °C

2.1: methanesulfonamide; K₂CO₃; (DHQ)2PYR / K₂OsO₄*2H₂O; K₃[Fe(CN)6] / H₂O; 2-methyl-propan-2-ol / 48 h / 20 °C

3.1: 85 percent / pTsOH / acetone / 2 h / 20 °C

4.1: 0.124 g / NaHCO₃; Selectfluor / acetonitrile / 72 h / 20 °C

With (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); N,N,N,N,-tetramethylethylenediamine; methanesulfonamide; sec.-butyllithium; sodium hydrogencarbonate; potassium carbonate; Selectfluor; potassium osmate(VI); toluene-4-sulfonic acid; potassium hexacyanoferrate(III); In tetrahydrofuran; water; acetone; acetonitrile; tert-butyl alcohol; 2.1: Sharpless dihydroxylation;

DOI:10.1002/chem.200600861

Reference yield:

cyclohexa-2,5-dien-1-yl(trimethyl)silane (54380-53-9) → (3S,5S,7R)-5-fluoro-2,2-dimethyl-3,4,5,7-tetrahydro-1,3-benzodioxole (927682-02-8)

Guidance literature:

Multi-step reaction with 3 steps

1: methanesulfonamide; K₂CO₃; (DHQ)2PYR / K₂OsO₄*2H₂O; K₃[Fe(CN)6] / H₂O; 2-methyl-propan-2-ol / 48 h / 20 °C

2: 85 percent / pTsOH / acetone / 2 h / 20 °C

3: 0.124 g / NaHCO₃; Selectfluor / acetonitrile / 72 h / 20 °C

With (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); methanesulfonamide; sodium hydrogencarbonate; potassium carbonate; Selectfluor; potassium osmate(VI); toluene-4-sulfonic acid; potassium hexacyanoferrate(III); In water; acetone; acetonitrile; tert-butyl alcohol; 1: Sharpless dihydroxylation;

DOI:10.1002/chem.200600861

upstream raw materials:

(3S,4S,7S)-2,2-dimethyl-3,4,7-tetrahydro-1,3-benzodioxol-4-yl(trimethyl)silane

cyclohexa-1,4-diene

cyclohexa-2,5-dien-1-yl(trimethyl)silane

(1S,2S,3S)-3-(trimethylsilyl)cyclohexane-4-ene-1,2-diol