(2R,4S,5R,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-5-(tert-butyldimethylsilanyloxymethyl)-5-methyl-4-triethylsilanyloxytetrahydropyran-2-ylmethyl benzoate

Base Information

• Chemical Name: (2R,4S,5R,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-5-(tert-butyldimethylsilanyloxymethyl)-5-methyl-4-triethylsilanyloxytetrahydropyran-2-ylmethyl benzoate
• CAS No.: 635727-25-2
• Molecular Formula: C₃₅H₆₆O₆Si₃
• Molecular Weight: 667.162
• Mol file: 635727-25-2.mol

Synonyms:(2R,4S,5R,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-5-(tert-butyldimethylsilanyloxymethyl)-5-methyl-4-triethylsilanyloxytetrahydropyran-2-ylmethyl benzoate

Chemical Property of (2R,4S,5R,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-5-(tert-butyldimethylsilanyloxymethyl)-5-methyl-4-triethylsilanyloxytetrahydropyran-2-ylmethyl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S,5R,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-5-(tert-butyldimethylsilanyloxymethyl)-5-methyl-4-triethylsilanyloxytetrahydropyran-2-ylmethyl benzoate

There total 14 articles about (2R,4S,5R,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-5-(tert-butyldimethylsilanyloxymethyl)-5-methyl-4-triethylsilanyloxytetrahydropyran-2-ylmethyl benzoate 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: 98.0%

triethylsilyl trifluoromethyl sulfonate (79271-56-0) + benzoic acid 6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester (635727-24-1) → (2R,4S,5R,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-5-(tert-butyldimethylsilanyloxymethyl)-5-methyl-4-triethylsilanyloxytetrahydropyran-2-ylmethyl benzoate (635727-25-2)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1055/s-2004-822340

Reference yield:

(2R,4aR,5R,7R)-5-allyl-7-iodomethyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxane (635727-03-6) → (2R,4S,5R,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-5-(tert-butyldimethylsilanyloxymethyl)-5-methyl-4-triethylsilanyloxytetrahydropyran-2-ylmethyl benzoate (635727-25-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 97 percent / 1-methyl-pyrrolidin-2-one / 6 h / 100 °C

2.1: O₃; NaHCO₃ / methanol / -78 °C

2.2: Me₂S / methanol / 0.5 h / 0 °C

3.1: 313 mg / NaBH₄ / methanol / 0.5 h / 0 °C

4.1: 89 percent / H₂; AcOH / Pd/C / methanol / 3 h / 20 °C / atmospheric pressure

5.1: 95 percent / imidazole / dimethylformamide / 3 h / 0 °C

6.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; hydrogen; sodium hydrogencarbonate; ozone; acetic acid; palladium on activated charcoal; In 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-2004-822340

Reference yield:

(2R,4aR,5R,7R)-5-allyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxan-7-ylmethyl benzoate (635727-22-9) → (2R,4S,5R,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-5-(tert-butyldimethylsilanyloxymethyl)-5-methyl-4-triethylsilanyloxytetrahydropyran-2-ylmethyl benzoate (635727-25-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: O₃; NaHCO₃ / methanol / -78 °C

1.2: Me₂S / methanol / 0.5 h / 0 °C

2.1: 313 mg / NaBH₄ / methanol / 0.5 h / 0 °C

3.1: 89 percent / H₂; AcOH / Pd/C / methanol / 3 h / 20 °C / atmospheric pressure

4.1: 95 percent / imidazole / dimethylformamide / 3 h / 0 °C

5.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; hydrogen; sodium hydrogencarbonate; ozone; acetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-2004-822340

upstream raw materials:

triethylsilyl trifluoromethyl sulfonate

benzoic acid 6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

sodium benzoate

(2R,4aR,5R,7R)-5-allyl-7-iodomethyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxane