(3aS,4R,6R,6aS)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-fluoro-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxole

Base Information

• Chemical Name: (3aS,4R,6R,6aS)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-fluoro-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxole
• CAS No.: 94898-41-6
• Molecular Formula: C₁₂H₁₉FO₅
• Molecular Weight: 262.278
• Mol file: 94898-41-6.mol

Synonyms:(3aS,4R,6R,6aS)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-fluoro-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxole

Chemical Property of (3aS,4R,6R,6aS)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-fluoro-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4R,6R,6aS)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-fluoro-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxole

There total 1 articles about (3aS,4R,6R,6aS)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-fluoro-2,2-dimethyl-tetrahydrofuro[3,4-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: 57.0%

2,3,5,6-di-O-isopropylidene-D-mannofuranose (7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4) → (3aS,4R,6R,6aS)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-fluoro-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxole (94898-41-6) + triphenylphosphine oxide-trifluoroborane

Guidance literature:

With triethyloxonium fluoroborate; triphenylphosphine; diethylazodicarboxylate; In dichloromethane; at -78 ℃; for 4h;

DOI:10.1002/hlca.19850680134

Reference yield: 54.0%

benzyloxy-trimethylsilane (14642-79-6) + (3aS,4R,6R,6aS)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-fluoro-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxole (94898-41-6) → phenylmethyl 2,3:5,6-di-O-(1-methylethylidene)-α-D-mannofuranoside (54469-08-8,74912-00-8,74912-01-9,20689-02-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 0.166667h;

DOI:10.1002/hlca.19850680134

Reference yield:

(3aS,4R,6R,6aS)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-fluoro-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxole (94898-41-6) → (2S,3R,4S,5R)-5-(1-benzyl-1H-1,2,3-triazol-4-yl)-N,3,4-trihydroxytetrahydrofuran-2-carboxamide

Guidance literature:

Multi-step reaction with 8 steps

1: boron trifluoride diethyl etherate / acetonitrile / 2 h / 0 °C

2: toluene-4-sulfonic acid; methanol / 16 h / 20 °C

3: [bis(acetoxy)iodo]benzene / dichloromethane / 0.75 h / 20 °C / Inert atmosphere

4: chromium(VI) oxide; sulfuric acid; water / acetonitrile / 3 h / 20 °C

5: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C

6: erbium(III) triflate / methanol / 1 h / 110 °C / 5171.62 Torr / Microwave irradiation

7: sodium L-ascorbate; copper(ll) sulfate pentahydrate / tert-butyl alcohol; water / 24 h / 20 °C

8: hydroxylamine hydrochloride; sodium methylate / methanol / 20 h / 20 °C

With chromium(VI) oxide; methanol; copper(ll) sulfate pentahydrate; [bis(acetoxy)iodo]benzene; sulfuric acid; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; water; sodium methylate; potassium carbonate; toluene-4-sulfonic acid; sodium L-ascorbate; erbium(III) triflate; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 4: |Jones Oxidation / 7: |Huisgen Cycloaddition;

DOI:10.1016/j.tet.2013.08.074

upstream raw materials:

2,3,5,6-di-O-isopropylidene-D-mannofuranose

Downstream raw materials:

phenylmethyl 2,3:5,6-di-O-(1-methylethylidene)-α-D-mannofuranoside

2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyl cyanide

2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl cyanide

2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyl isocyanide