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

Base Information

• Chemical Name: ((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl trifluoromethanesulphonate
• CAS No.: 895558-57-3
• Molecular Formula: C₁₆H₁₉F₃O₇S
• Molecular Weight: 412.384
• Mol file: 895558-57-3.mol

Synonyms:((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl trifluoromethanesulphonate

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about ((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl trifluoromethanesulphonate 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: 93.0%

trifluoromethylsulfonic anhydride (358-23-6) + ((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,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl trifluoromethanesulphonate (895558-57-3)

Guidance literature:

With pyridine; In dichloromethane; at -30 ℃; for 0.25h;

DOI:10.1021/ja052929v

Reference yield:

5-O-p-toluenesulfonyl-3-O-benzyl-1,2-O-isopropylidene-β-D-arabinofuranose (40429-53-6) → ((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl trifluoromethanesulphonate (895558-57-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / 4percent Na(Hg) / methanol; H₂O / 3 h

2: pyridine / CH₂Cl₂ / 0.25 h / -30 °C

With pyridine; sodium amalgam; In methanol; dichloromethane; water;

DOI:10.1021/ja00065a042

Reference yield:

1,2-O-isopropylidene-5-O-toluene-p-sulphonyl-β-D-arabinofuranose (40429-51-4) → ((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl trifluoromethanesulphonate (895558-57-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / NaH / dimethylformamide / 0.25 h / Ambient temperature

2: 94 percent / 4percent Na(Hg) / methanol; H₂O / 3 h

3: pyridine / CH₂Cl₂ / 0.25 h / -30 °C

With pyridine; sodium amalgam; sodium hydride; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja00065a042

upstream raw materials:

trifluoromethylsulfonic anhydride

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

5-O-p-toluenesulfonyl-3-O-benzyl-1,2-O-isopropylidene-β-D-arabinofuranose

1,2-O-isopropylidene-5-O-toluene-p-sulphonyl-β-D-arabinofuranose

Downstream raw materials:

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

Benzoic acid (2R,3S)-2,3-bis-benzyloxy-3-(2-fluoromethyl-[1,3]dioxan-2-yl)-propyl ester

Phosphoric acid (2R,3S)-2,3-bis-benzyloxy-3-(2-fluoromethyl-[1,3]dioxan-2-yl)-propyl ester dimethyl ester

1-deoxy-1-fluoro-3,4-di-O-benzyl-5-O-benzoyl-D-lyxitol