(1R,5R,6R,7R)-6-<(benzoyloxy)methyl>-7-<<3-(trifluoromethyl)benzoyl>oxy>-2,8-dioxabicyclo<3.2.1>octane

Base Information

• Chemical Name: (1R,5R,6R,7R)-6-<(benzoyloxy)methyl>-7-<<3-(trifluoromethyl)benzoyl>oxy>-2,8-dioxabicyclo<3.2.1>octane
• CAS No.: 134056-17-0
• Molecular Formula: C₂₂H₁₉F₃O₆
• Molecular Weight: 436.384

Synonyms:(1R,5R,6R,7R)-6-<(benzoyloxy)methyl>-7-<<3-(trifluoromethyl)benzoyl>oxy>-2,8-dioxabicyclo<3.2.1>octane

Chemical Property of (1R,5R,6R,7R)-6-<(benzoyloxy)methyl>-7-<<3-(trifluoromethyl)benzoyl>oxy>-2,8-dioxabicyclo<3.2.1>octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,5R,6R,7R)-6-<(benzoyloxy)methyl>-7-<<3-(trifluoromethyl)benzoyl>oxy>-2,8-dioxabicyclo<3.2.1>octane

There total 9 articles about (1R,5R,6R,7R)-6-<(benzoyloxy)methyl>-7-<<3-(trifluoromethyl)benzoyl>oxy>-2,8-dioxabicyclo<3.2.1>octane 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: 88.0%

3-(Trifluoromethyl)benzoyl chloride (2251-65-2) + (1R,5R,6R,7R)-6-<(benzoyloxy)methyl>-7-hydroxy-2,8-dioxabicyclo<3.2.1>octane (134056-16-9) → (1R,5R,6R,7R)-6-<(benzoyloxy)methyl>-7-<<3-(trifluoromethyl)benzoyl>oxy>-2,8-dioxabicyclo<3.2.1>octane (134056-17-0)

Guidance literature:

With pyridine; dmap; for 3h; Ambient temperature;

DOI:10.1021/jo00012a018

Reference yield:

((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol (69832-48-0) → (1R,5R,6R,7R)-6-<(benzoyloxy)methyl>-7-<<3-(trifluoromethyl)benzoyl>oxy>-2,8-dioxabicyclo<3.2.1>octane (134056-17-0)

Guidance literature:

Multi-step reaction with 8 steps

1: pyridine / DMAP / 23 h / Ambient temperature

2: 1.6percent H₂SO₄ / methanol; CHCl₃ / 84 h

3: pyridine / 2 h / Ambient temperature

4: NaI / butan-2-one / 15 h / Heating

5: 1) BH₃*Me₂S, 2) NaHCO₃, 30percent H₂O₂ / 1a) THF, 0-4 deg C, 24 h, b) THF, methanol, 0 deg C, 1 h, 2) THF, methanol, water, up to r. t., 2 h

6: acidic cation-exchange resin (Dowex 50 W₈) / methanol / 5.5 h / Heating

7: acidic cation-exchange resin (Dowex 50 W₈) / toluene / 0.25 h / Heating

8: 88 percent / pyridine / DMAP / 3 h / Ambient temperature

With pyridine; dimethylsulfide borane complex; acidic cation-exchange resin (Dowex 50 W₈); sulfuric acid; dihydrogen peroxide; sodium hydrogencarbonate; sodium iodide; dmap; In methanol; chloroform; toluene; butanone;

DOI:10.1021/jo00012a018

Reference yield:

3-deoxy-3-<(benzoyloxy)methyl>-1,2-O-isopropylidene-α-D-allofuranose (130495-83-9) → (1R,5R,6R,7R)-6-<(benzoyloxy)methyl>-7-<<3-(trifluoromethyl)benzoyl>oxy>-2,8-dioxabicyclo<3.2.1>octane (134056-17-0)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / 2 h / Ambient temperature

2: NaI / butan-2-one / 15 h / Heating

3: 1) BH₃*Me₂S, 2) NaHCO₃, 30percent H₂O₂ / 1a) THF, 0-4 deg C, 24 h, b) THF, methanol, 0 deg C, 1 h, 2) THF, methanol, water, up to r. t., 2 h

4: acidic cation-exchange resin (Dowex 50 W₈) / methanol / 5.5 h / Heating

5: acidic cation-exchange resin (Dowex 50 W₈) / toluene / 0.25 h / Heating

6: 88 percent / pyridine / DMAP / 3 h / Ambient temperature

With pyridine; dimethylsulfide borane complex; acidic cation-exchange resin (Dowex 50 W₈); dihydrogen peroxide; sodium hydrogencarbonate; sodium iodide; dmap; In methanol; toluene; butanone;

DOI:10.1021/jo00012a018

upstream raw materials:

3-(Trifluoromethyl)benzoyl chloride

(1R,5R,6R,7R)-6-<(benzoyloxy)methyl>-7-hydroxy-2,8-dioxabicyclo<3.2.1>octane

((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol

3-deoxy-3-<(benzoyloxy)methyl>-1,2-O-isopropylidene-α-D-allofuranose

Downstream raw materials:

(1R,5R,6R)-6-<(benzoyloxy)methyl>-2,8-dioxabicyclo-<3.2.1>octane

1-<(2R,3R,4R,5R)-3-<<3-(trifluoromethyl)benzoyl>oxy>-4-<(benzoyloxy)methyl>-5-(2-hydroxyethyl)tetrahydrofuran-2-yl>uracil

N⁴-isobutyryl-1-{(2R,3R,4R,5R)-4-benzoyloxymethyl-5-(2-hydroxyethyl)-3-[(m-trifluoromethyl)benzoyloxy]tetrahydrofuran-2-yl}cytosine

9-{(2R,3R,4R,5R)-4-benzoyloxymethyl-5-(2-hydroxyethyl)-3-[(m-trifluoromethyl)benzoyloxy]tetrahydrofuran-2-yl}adenine

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