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

Base Information

Chemical Name:(R)-3-Benzyloxy-3-[(2S,3R,6S)-6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-propionaldehyde
CAS No.:419549-20-5
Molecular Formula:C₃₉H₄₆O₅Si
Molecular Weight:622.877
Hs Code.:

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

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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]-propionaldehyde

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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]-propionaldehyde

There total 14 articles about (R)-3-Benzyloxy-3-[(2S,3R,6S)-6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-propionaldehyde 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: 92.0%

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

: 419549-20-5
(R)-3-Benzyloxy-3-[(2S,3R,6S)-6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-propionaldehyde

Guidance literature:: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 20 ℃; for 5h;
DOI:10.1021/ol0256264

Reference yield:

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

: 419549-20-5
(R)-3-Benzyloxy-3-[(2S,3R,6S)-6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-propionaldehyde

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

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

8.1: 92 percent / IBX / dimethylsulfoxide / 5 h / 20 °C

With potassium hydroxide; disodium hydrogenphosphate; n-butyllithium; (1S)-10-camphorsulfonic acid; 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; toluene;
DOI:10.1021/ol0256264

Reference yield:

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

: 419549-20-5
(R)-3-Benzyloxy-3-[(2S,3R,6S)-6-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-propionaldehyde

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

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

7.1: 92 percent / IBX / dimethylsulfoxide / 5 h / 20 °C

With disodium hydrogenphosphate; n-butyllithium; (1S)-10-camphorsulfonic acid; 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; toluene;
DOI:10.1021/ol0256264