Benzoic acid (3aR,5R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-5-((4S,5R)-5-formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester

Base Information

• Chemical Name: Benzoic acid (3aR,5R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-5-((4S,5R)-5-formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester
• CAS No.: 118893-72-4
• Molecular Formula: C₂₇H₄₀O₉Si
• Molecular Weight: 536.695
• Mol file: 118893-72-4.mol

Synonyms:Benzoic acid (3aR,5R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-5-((4S,5R)-5-formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester

Chemical Property of Benzoic acid (3aR,5R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-5-((4S,5R)-5-formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (3aR,5R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-5-((4S,5R)-5-formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester

There total 4 articles about Benzoic acid (3aR,5R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-5-((4S,5R)-5-formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-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: 73.0%

Benzoic acid (3aR,5R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-5-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester (118893-71-3) → Benzoic acid (3aR,5R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-5-((4S,5R)-5-formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester (118893-72-4)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1021/ja00188a038

Reference yield:

Benzoic acid (3S,4R,5R)-2-((R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-tetrahydro-pyran-3-yl ester (118893-70-2,119007-06-6) → Benzoic acid (3aR,5R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-5-((4S,5R)-5-formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester (118893-72-4)

Guidance literature:

Multi-step reaction with 3 steps

1: conc. sulfuric acid, MgSO₄ / 12 h / 50 °C

2: 93 percent / H₂ / 20percent Pd(OH)2/C / ethanol / 5 h / 760 Torr

3: 73 percent / oxalyl chloride, dimethyl sulfoxide, triethylamine / CH₂Cl₂ / 0.5 h / -78 °C

With oxalyl dichloride; sulfuric acid; hydrogen; magnesium sulfate; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In ethanol; dichloromethane;

DOI:10.1021/ja00188a038

Reference yield:

Benzoic acid (3aR,5R,6S,7S,7aR)-5-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester (118893-69-9) → Benzoic acid (3aR,5R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-5-((4S,5R)-5-formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester (118893-72-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / H₂ / 20percent Pd(OH)2/C / ethanol / 5 h / 760 Torr

2: 73 percent / oxalyl chloride, dimethyl sulfoxide, triethylamine / CH₂Cl₂ / 0.5 h / -78 °C

With oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In ethanol; dichloromethane;

DOI:10.1021/ja00188a038

upstream raw materials:

Benzoic acid (3aR,5R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-5-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester

Benzoic acid (3S,4R,5R)-2-((R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-tetrahydro-pyran-3-yl ester

Benzoic acid (3aR,5R,6S,7S,7aR)-5-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester

Benzoic acid (3S,4R,5R)-2-((R)-3-benzyloxy-1,2-dihydroxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-tetrahydro-pyran-3-yl ester

Downstream raw materials:

C₄₅H₆₆O₁₃Si₂

C₄₅H₆₆O₁₃Si₂