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

Base Information

• Chemical Name: benzoic acid 6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 635727-24-1
• Molecular Formula: C₂₉H₅₂O₆Si₂
• Molecular Weight: 552.899
• Mol file: 635727-24-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about benzoic acid 6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-5-methyl-tetrahydro-pyran-2-ylmethyl 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: 95.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2R,4S,5S,6R)-4-hydroxy-6-(2-hydroxyethyl)-5-hydroxymethyl-5-methyltetrahydropyran-2-ylmethyl benzoate (635727-04-7) → 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)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 3h;

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) → 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)

Guidance literature:

Multi-step reaction with 5 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

With 1H-imidazole; sodium tetrahydroborate; hydrogen; sodium hydrogencarbonate; ozone; acetic acid; palladium on activated charcoal; In 1-methyl-pyrrolidin-2-one; methanol; 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) → 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)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1055/s-2004-822340

upstream raw materials:

tert-butyldimethylsilyl chloride

(2R,4S,5S,6R)-4-hydroxy-6-(2-hydroxyethyl)-5-hydroxymethyl-5-methyltetrahydropyran-2-ylmethyl benzoate

sodium benzoate

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

Downstream raw materials:

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