(R)-3-Benzyloxy-3-[(2S,3R,6S)-6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-propan-1-ol

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Chemical Name:(R)-3-Benzyloxy-3-[(2S,3R,6S)-6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-propan-1-ol
CAS No.:419549-18-1
Molecular Formula:C₃₉H₄₈O₅Si
Molecular Weight:624.893
Hs Code.:

Synonyms:(R)-3-Benzyloxy-3-[(2S,3R,6S)-6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-propan-1-ol

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Chemical Property of (R)-3-Benzyloxy-3-[(2S,3R,6S)-6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-propan-1-ol

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Technology Process of (R)-3-Benzyloxy-3-[(2S,3R,6S)-6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-propan-1-ol

There total 13 articles about (R)-3-Benzyloxy-3-[(2S,3R,6S)-6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-propan-1-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:

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

: 419549-18-1
(R)-3-Benzyloxy-3-[(2S,3R,6S)-6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-propan-1-ol

Guidance literature:: Multi-step reaction with 7 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: 10-camphorsulfonic acid / CH₂Cl₂ / 14 h / 20 °C

7.2: 525 mg / BH₃*THF / tetrahydrofuran / 7 h / Heating

With potassium hydroxide; disodium hydrogenphosphate; n-butyllithium; (1S)-10-camphorsulfonic acid; hydrogen; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene;
DOI:10.1021/ol0256264

Reference yield:

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

: 419549-18-1
(R)-3-Benzyloxy-3-[(2S,3R,6S)-6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-propan-1-ol

Guidance literature:: Multi-step reaction with 6 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: 10-camphorsulfonic acid / CH₂Cl₂ / 14 h / 20 °C

6.2: 525 mg / BH₃*THF / tetrahydrofuran / 7 h / Heating

With disodium hydrogenphosphate; n-butyllithium; (1S)-10-camphorsulfonic acid; hydrogen; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene;
DOI:10.1021/ol0256264

Reference yield:

: 152388-66-4
((2S,5R,6R)-5-hydroxy-6-((trimethylsilyl)ethynyl)-5,6-dihydro-2H-pyran-2-yl)methyl ethanoate

: 419549-18-1
(R)-3-Benzyloxy-3-[(2S,3R,6S)-6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-propan-1-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 100 percent / imidazole / dimethylformamide

2.1: Co₂(CO)8 / CH₂Cl₂ / 20 °C

2.2: BF₃*Et₂O / CH₂Cl₂ / 0 - 20 °C

2.3: 92 percent / I₂ / tetrahydrofuran

3.1: 99 percent / K₂CO₃ / methanol / 2 h / 20 °C

4.1: 87 percent / KOH / 2 h / 90 °C

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

5.2: 55 percent / tetrahydrofuran; hexane / 17 h / -78 - 0 °C

6.1: 95 percent / Red-Al(R) / tetrahydrofuran; toluene / 0.58 h / 0 - 20 °C

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

8.1: 1.92 g / Red-Al(R) / toluene / 1.5 h / 0 °C

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

10.1: 10-camphorsulfonic acid / CH₂Cl₂ / 14 h / 20 °C

10.2: 525 mg / BH₃*THF / tetrahydrofuran / 7 h / Heating

With 1H-imidazole; potassium hydroxide; disodium hydrogenphosphate; n-butyllithium; dicobalt octacarbonyl; (1S)-10-camphorsulfonic acid; hydrogen; sodium hydrogencarbonate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol0256264