Trifluoro-methanesulfonic acid (3R,4R,5R)-4-benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2-oxo-tetrahydro-furan-3-yl ester

Base Information

Chemical Name:Trifluoro-methanesulfonic acid (3R,4R,5R)-4-benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2-oxo-tetrahydro-furan-3-yl ester
CAS No.:217089-55-9
Molecular Formula:C₂₁H₂₁F₃O₈S
Molecular Weight:490.454
Hs Code.:

Synonyms:Trifluoro-methanesulfonic acid (3R,4R,5R)-4-benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2-oxo-tetrahydro-furan-3-yl ester

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Chemical Property of Trifluoro-methanesulfonic acid (3R,4R,5R)-4-benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2-oxo-tetrahydro-furan-3-yl ester

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Technology Process of Trifluoro-methanesulfonic acid (3R,4R,5R)-4-benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2-oxo-tetrahydro-furan-3-yl ester

There total 8 articles about Trifluoro-methanesulfonic acid (3R,4R,5R)-4-benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2-oxo-tetrahydro-furan-3-yl ester 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%

: 217089-53-7
Trifluoro-methanesulfonic acid (3R,4R,5R)-4-benzyloxy-5-[(R)-1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-tetrahydro-furan-3-yl ester

: 217089-55-9
Trifluoro-methanesulfonic acid (3R,4R,5R)-4-benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2-oxo-tetrahydro-furan-3-yl ester

Guidance literature:: With trifluoroacetic acid; In 1,4-dioxane; water; for 0.25h; Ambient temperature;
DOI:10.1016/S0040-4020(98)00837-0

Reference yield:

: 4495-04-9
1,2-O-isopropylidene-α-D-allofuranose

: 217089-55-9
Trifluoro-methanesulfonic acid (3R,4R,5R)-4-benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2-oxo-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / imidazole / dimethylformamide / 2 h / -20 °C

2: 1.) NaH, 2.) n-Bu₄NI / 1.) DMF, 1 h, 2.) room temperature, 26 h

3: 82 percent / TFA / dioxane; H₂O / 45 h / Ambient temperature

4: 90 percent / BaCO₃, Br₂ / dioxane; H₂O / 2 h / Ambient temperature

5: 41 percent / imidazole / dimethylformamide / 2 h / -65 °C

6: pyridine / 1 h / -50 °C

7: 86 percent / TFA / dioxane; H₂O / 0.25 h / Ambient temperature

With pyridine; 1H-imidazole; bromine; tetra-(n-butyl)ammonium iodide; sodium hydride; barium carbonate; trifluoroacetic acid; In 1,4-dioxane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(98)00837-0

Reference yield:

: 2847-00-9
1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

: 217089-55-9
Trifluoro-methanesulfonic acid (3R,4R,5R)-4-benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2-oxo-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: NaBH₄ / ethanol; H₂O / 1 h / 0 °C

2: 98 percent / AcOH / H₂O / 16 h / Ambient temperature

3: 98 percent / imidazole / dimethylformamide / 2 h / -20 °C

4: 1.) NaH, 2.) n-Bu₄NI / 1.) DMF, 1 h, 2.) room temperature, 26 h

5: 82 percent / TFA / dioxane; H₂O / 45 h / Ambient temperature

6: 90 percent / BaCO₃, Br₂ / dioxane; H₂O / 2 h / Ambient temperature

7: 41 percent / imidazole / dimethylformamide / 2 h / -65 °C

8: pyridine / 1 h / -50 °C

9: 86 percent / TFA / dioxane; H₂O / 0.25 h / Ambient temperature

With pyridine; 1H-imidazole; sodium tetrahydroborate; bromine; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; barium carbonate; trifluoroacetic acid; In 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(98)00837-0