3a-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

Base Information

Chemical Name:3a-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol
CAS No.:579505-76-3
Molecular Formula:C₂₅H₃₂O₄Si
Molecular Weight:424.612
Hs Code.:

3a-(<i>tert</i>-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-4,6a-dihydro-3a<i>H</i>-cyclopenta[1,3]dioxol-4-ol

Synonyms:3a-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

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Chemical Property of 3a-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

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Technology Process of 3a-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

There total 9 articles about 3a-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol 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: 84.0%

: 579505-75-2
1-[(4R,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl]-prop-2-en-1-ol

: 579505-76-3
3a-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

Guidance literature:: Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 6h;
DOI:10.1016/S0040-4039(03)01132-8

Reference yield:

: 7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4
2,3,5,6-di-O-isopropylidene-D-mannofuranose

: 579505-76-3
3a-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 85 percent / K₂CO₃ / methanol / 48 h / 85 °C

2.1: 79 percent / imidazole / DMAP / CH₂Cl₂ / 6 h / 0 - 20 °C

3.1: 91 percent / NaH / DMAP / tetrahydrofuran / 3 h / 0 - 20 °C

4.1: 73 percent / AcOH; water / 24 h / 20 °C

5.1: NaIO₄ / tetrahydrofuran; H₂O / 6 h / 0 - 20 °C

5.2: 82 percent / NaBH₄ / methanol / 0.5 h / 0 - 20 °C

6.1: 76 percent / I₂; PPh₃; imidazole / toluene / 8 h / 120 °C

7.1: Zn / tetrahydrofuran; H₂O / 5 h / 20 - 50 °C / sonication

8.1: tetrahydrofuran / 2 h / 0 °C

9.1: 84 percent / Grubbs' catalyst / CH₂Cl₂ / 6 h / 20 °C

With 1H-imidazole; sodium periodate; water; iodine; sodium hydride; potassium carbonate; acetic acid; triphenylphosphine; zinc; dmap; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; water; toluene;
DOI:10.1016/S0040-4039(03)01132-8

Reference yield:

: (3aS,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3a-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol

: 579505-76-3
3a-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 79 percent / imidazole / DMAP / CH₂Cl₂ / 6 h / 0 - 20 °C

2.1: 91 percent / NaH / DMAP / tetrahydrofuran / 3 h / 0 - 20 °C

3.1: 73 percent / AcOH; water / 24 h / 20 °C

4.1: NaIO₄ / tetrahydrofuran; H₂O / 6 h / 0 - 20 °C

4.2: 82 percent / NaBH₄ / methanol / 0.5 h / 0 - 20 °C

5.1: 76 percent / I₂; PPh₃; imidazole / toluene / 8 h / 120 °C

6.1: Zn / tetrahydrofuran; H₂O / 5 h / 20 - 50 °C / sonication

7.1: tetrahydrofuran / 2 h / 0 °C

8.1: 84 percent / Grubbs' catalyst / CH₂Cl₂ / 6 h / 20 °C

With 1H-imidazole; sodium periodate; water; iodine; sodium hydride; acetic acid; triphenylphosphine; zinc; dmap; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; water; toluene;
DOI:10.1016/S0040-4039(03)01132-8