Benzoic 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:Benzoic 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.:199338-66-4
Molecular Formula:C₂₆H₄₀O₇Si
Molecular Weight:492.685
Hs Code.:

Benzoic 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

Synonyms:Benzoic 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

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Chemical Property of Benzoic 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

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Technology Process of Benzoic 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 12 articles about Benzoic 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:

: 98-88-4
benzoyl chloride

: 199338-64-2
[(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

: 199338-66-4
Benzoic 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

Guidance literature:: With dmap; triethylamine; In dichloromethane; Ambient temperature;
DOI:10.1021/jo971701q

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 199338-64-2
[(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

: 199338-66-4
Benzoic 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

Guidance literature:: With pyridine; dmap; In dichloromethane; at 0 - 20 ℃; for 0.5h;

Reference yield:

: 32384-42-2
(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone

: 199338-66-4
Benzoic 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

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: Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; osmium(VIII) oxide; camphor-10-sulfonic acid; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; 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: benzoylation;
DOI:10.1021/jo9908849