(3aR,5R,6S,7S,7aR)-7-(tert-Butyl-diphenyl-silanyloxy)-2,2-diethyl-5,6-dihydroxy-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

Base Information

Chemical Name:(3aR,5R,6S,7S,7aR)-7-(tert-Butyl-diphenyl-silanyloxy)-2,2-diethyl-5,6-dihydroxy-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester
CAS No.:244231-03-6
Molecular Formula:C₂₉H₄₀O₇Si
Molecular Weight:528.718
Hs Code.:

Synonyms:(3aR,5R,6S,7S,7aR)-7-(tert-Butyl-diphenyl-silanyloxy)-2,2-diethyl-5,6-dihydroxy-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

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Chemical Property of (3aR,5R,6S,7S,7aR)-7-(tert-Butyl-diphenyl-silanyloxy)-2,2-diethyl-5,6-dihydroxy-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

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Technology Process of (3aR,5R,6S,7S,7aR)-7-(tert-Butyl-diphenyl-silanyloxy)-2,2-diethyl-5,6-dihydroxy-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

There total 9 articles about (3aR,5R,6S,7S,7aR)-7-(tert-Butyl-diphenyl-silanyloxy)-2,2-diethyl-5,6-dihydroxy-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl 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: 93.0%

: 244231-02-5
(3aR,7S,7aR)-7-(tert-Butyl-diphenyl-silanyloxy)-2,2-diethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

: 244231-03-6
(3aR,5R,6S,7S,7aR)-7-(tert-Butyl-diphenyl-silanyloxy)-2,2-diethyl-5,6-dihydroxy-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In pyridine; water; tert-butyl alcohol; for 3h; Heating;
DOI:10.1021/jo9908849

Reference yield:

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

: 244231-03-6
(3aR,5R,6S,7S,7aR)-7-(tert-Butyl-diphenyl-silanyloxy)-2,2-diethyl-5,6-dihydroxy-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 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 / dimethylformamide / 5 h / 20 °C

5: 80 percent AcOH / H₂O / 2 h / 50 °C

6: 96 percent / camphorsulfonic acid / CH₂Cl₂ / 0.5 h / 20 °C

7: 93 percent / N-methylmorpholine N-oxide; OsO₄ / pyridine; H₂O; 2-methyl-propan-2-ol / 3 h / Heating

With 1H-imidazole; dmap; sodium tetrahydroborate; osmium(VIII) oxide; camphor-10-sulfonic acid; acetic acid; 4-methylmorpholine N-oxide; pyridinium chlorochromate; In pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: methanolysis / 2: Oxidation / 3: Reduction / 4: Etherification / 5: deketalization / 6: ketalization / 7: dihydroxylation;
DOI:10.1021/jo9908849

Reference yield:

: 77-95-2
D-(-)-quinic acid

: 244231-03-6
(3aR,5R,6S,7S,7aR)-7-(tert-Butyl-diphenyl-silanyloxy)-2,2-diethyl-5,6-dihydroxy-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 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 / dimethylformamide / 5 h / 20 °C

6: 80 percent AcOH / H₂O / 2 h / 50 °C

7: 96 percent / camphorsulfonic acid / CH₂Cl₂ / 0.5 h / 20 °C

8: 93 percent / N-methylmorpholine N-oxide; OsO₄ / pyridine; H₂O; 2-methyl-propan-2-ol / 3 h / Heating

With 1H-imidazole; dmap; sodium tetrahydroborate; osmium(VIII) oxide; camphor-10-sulfonic acid; toluene-4-sulfonic acid; acetic acid; 4-methylmorpholine N-oxide; pyridinium chlorochromate; In pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 1: Cyclization / 2: methanolysis / 3: Oxidation / 4: Reduction / 5: Etherification / 6: deketalization / 7: ketalization / 8: dihydroxylation;
DOI:10.1021/jo9908849