Toluene-4-sulfonic acid (3aS,4aR,7aR,8R,8aS)-8-(tert-butyl-dimethyl-silanyloxy)-2,2,6,6-tetramethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-3a-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (3aS,4aR,7aR,8R,8aS)-8-(tert-butyl-dimethyl-silanyloxy)-2,2,6,6-tetramethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-3a-ylmethyl ester
• CAS No.: 199338-67-5
• Molecular Formula: C₂₆H₄₂O₈SSi
• Molecular Weight: 542.766
• Mol file: 199338-67-5.mol

Synonyms:Toluene-4-sulfonic acid (3aS,4aR,7aR,8R,8aS)-8-(tert-butyl-dimethyl-silanyloxy)-2,2,6,6-tetramethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-3a-ylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (3aS,4aR,7aR,8R,8aS)-8-(tert-butyl-dimethyl-silanyloxy)-2,2,6,6-tetramethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-3a-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (3aS,4aR,7aR,8R,8aS)-8-(tert-butyl-dimethyl-silanyloxy)-2,2,6,6-tetramethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-3a-ylmethyl ester

There total 11 articles about Toluene-4-sulfonic acid (3aS,4aR,7aR,8R,8aS)-8-(tert-butyl-dimethyl-silanyloxy)-2,2,6,6-tetramethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-3a-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:

p-toluenesulfonyl chloride (98-59-9) + [(3aS,4aR,7aR,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-2,2,6,6-tetramethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-3a-yl]-methanol (199338-64-2) → Toluene-4-sulfonic acid (3aS,4aR,7aR,8R,8aS)-8-(tert-butyl-dimethyl-silanyloxy)-2,2,6,6-tetramethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-3a-ylmethyl ester (199338-67-5)

Guidance literature:

With dmap; triethylamine; In dichloromethane; Ambient temperature;

DOI:10.1021/jo971701q

Reference yield:

(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone (32384-42-2) → Toluene-4-sulfonic acid (3aS,4aR,7aR,8R,8aS)-8-(tert-butyl-dimethyl-silanyloxy)-2,2,6,6-tetramethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-3a-ylmethyl ester (199338-67-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 82 percent / methanol / 5 h / 20 °C

2: 60 percent / PCC / pyridine; CH₂Cl₂ / 24 h / 20 °C

3: 98 percent / NaBH₄ / methanol / 0.5 h / 20 °C

4: imidazole; DMAP / CH₂Cl₂ / 2 h / 20 °C

5: 95 percent / N-methylmorpholine N-oxide; OsO₄ / pyridine; H₂O; 2-methyl-propan-2-ol / 3 h / Heating

6: 94 percent / camphorsulfonic acid / CH₂Cl₂ / 2 h / 20 °C

7: 92.3 percent / DIBAL-H / hexane; tetrahydrofuran / 2 h / 0 °C

8: DMAP / pyridine; CH₂Cl₂ / 30 h / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; osmium(VIII) oxide; camphor-10-sulfonic acid; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; pyridinium chlorochromate; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; tert-butyl alcohol; 1: methanolysis / 2: Oxidation / 3: Reduction / 4: Etherification / 5: dihydroxylation / 6: ketalization / 7: Reduction / 8: Tosylation;

DOI:10.1021/jo9908849

Reference yield:

D-(-)-quinic acid (77-95-2) → Toluene-4-sulfonic acid (3aS,4aR,7aR,8R,8aS)-8-(tert-butyl-dimethyl-silanyloxy)-2,2,6,6-tetramethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-3a-ylmethyl ester (199338-67-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 84 percent / p-TsOH / benzene / 15 h / Heating

2: 82 percent / methanol / 5 h / 20 °C

3: 60 percent / PCC / pyridine; CH₂Cl₂ / 24 h / 20 °C

4: 98 percent / NaBH₄ / methanol / 0.5 h / 20 °C

5: imidazole; DMAP / CH₂Cl₂ / 2 h / 20 °C

6: 95 percent / N-methylmorpholine N-oxide; OsO₄ / pyridine; H₂O; 2-methyl-propan-2-ol / 3 h / Heating

7: 94 percent / camphorsulfonic acid / CH₂Cl₂ / 2 h / 20 °C

8: 92.3 percent / DIBAL-H / hexane; tetrahydrofuran / 2 h / 0 °C

9: DMAP / pyridine; CH₂Cl₂ / 30 h / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; osmium(VIII) oxide; camphor-10-sulfonic acid; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; pyridinium chlorochromate; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; tert-butyl alcohol; benzene; 1: Cyclization / 2: methanolysis / 3: Oxidation / 4: Reduction / 5: Etherification / 6: dihydroxylation / 7: ketalization / 8: Reduction / 9: Tosylation;

DOI:10.1021/jo9908849

upstream raw materials:

p-toluenesulfonyl chloride

[(3aS,4aR,7aR,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-2,2,6,6-tetramethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-3a-yl]-methanol

(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone

D-(-)-quinic acid

Downstream raw materials:

Toluene-4-sulfonic acid (3aS,4aR,7aS,8R,8aS)-8-hydroxy-2,2,6,6-tetramethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-3a-ylmethyl ester