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

Base Information

• Chemical Name: 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
• CAS No.: 217089-53-7
• Molecular Formula: C₂₇H₃₅F₃O₈SSi
• Molecular Weight: 604.717

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 7 articles about 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 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:

1,2-O-isopropylidene-α-D-allofuranose (4495-04-9) → 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 (217089-53-7)

Guidance literature:

Multi-step reaction with 6 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

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:

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose (2847-00-9) → 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 (217089-53-7)

Guidance literature:

Multi-step reaction with 8 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

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

Reference yield:

(1,2:5,6)-di-O-isopropylidene-D-gulose (14686-89-6) → 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 (217089-53-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 98 percent / AcOH / H₂O / 16 h / Ambient temperature

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

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

4: 82 percent / TFA / dioxane; H₂O / 45 h / Ambient temperature

5: 90 percent / BaCO₃, Br₂ / dioxane; H₂O / 2 h / Ambient temperature

6: 41 percent / imidazole / dimethylformamide / 2 h / -65 °C

7: pyridine / 1 h / -50 °C

With pyridine; 1H-imidazole; bromine; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; barium carbonate; trifluoroacetic acid; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(98)00837-0

upstream raw materials:

trifluoromethylsulfonic anhydride

(3R,4S,5R)-4-Benzyloxy-5-[(R)-1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-dihydro-furan-2-one

1,2-O-isopropylidene-α-D-allofuranose

(1,2:5,6)-di-O-isopropylidene-D-gulose

Downstream raw materials:

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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