1-[6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propan-1-one

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Chemical Name:1-[6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propan-1-one
CAS No.:419549-42-1
Molecular Formula:C₃₈H₅₄O₅Si₂
Molecular Weight:647.015
Hs Code.:

1-[6-benzyloxymethyl-3-(<i>tert</i>-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-propan-1-one

Synonyms:1-[6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propan-1-one

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Chemical Property of 1-[6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propan-1-one

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Technology Process of 1-[6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propan-1-one

There total 12 articles about 1-[6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propan-1-one 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: 82.0%

: 419549-41-0
(S)-1-[(2S,3R,6S)-6-Benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propan-1-ol

: 419549-42-1
1-[6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propan-1-one

Guidance literature:: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide;
DOI:10.1021/ol0256264

Reference yield:

: [5-(tert-butyl-diphenyl-silanyloxy)-6-ethynyl-5,6-dihydro-2H-pyran-2-yl]-methanol

: 419549-42-1
1-[6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propan-1-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 87 percent / KOH / 2 h / 90 °C

2.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

2.2: 55 percent / tetrahydrofuran; hexane / 17 h / -78 - 0 °C

3.1: 95 percent / Red-Al(R) / tetrahydrofuran; toluene / 0.58 h / 0 - 20 °C

4.1: m-chloroperbenzoic acid; di-sodium hydrogenphosphate / CH₂Cl₂ / 14 h / 20 °C

5.1: 1.92 g / Red-Al(R) / toluene / 1.5 h / 0 °C

6.1: H₂; sodium hydrogen carbonate / Pd/C / ethanol / 4 h / 20 °C

7.1: 92 percent / imidazole / dimethylformamide

8.1: 82 percent / IBX / dimethylsulfoxide

With 1H-imidazole; potassium hydroxide; disodium hydrogenphosphate; n-butyllithium; hydrogen; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol0256264

Reference yield:

: (6-benzyloxymethyl-2-ethynyl-3,6-dihydro-2H-pyran-3-yloxy)-tert-butyl-diphenyl-silane

: 419549-42-1
1-[6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propan-1-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

1.2: 55 percent / tetrahydrofuran; hexane / 17 h / -78 - 0 °C

2.1: 95 percent / Red-Al(R) / tetrahydrofuran; toluene / 0.58 h / 0 - 20 °C

3.1: m-chloroperbenzoic acid; di-sodium hydrogenphosphate / CH₂Cl₂ / 14 h / 20 °C

4.1: 1.92 g / Red-Al(R) / toluene / 1.5 h / 0 °C

5.1: H₂; sodium hydrogen carbonate / Pd/C / ethanol / 4 h / 20 °C

6.1: 92 percent / imidazole / dimethylformamide

7.1: 82 percent / IBX / dimethylsulfoxide

With 1H-imidazole; disodium hydrogenphosphate; n-butyllithium; hydrogen; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol0256264