Acetic acid (2S,5R,6R)-5-(tert-butyl-diphenyl-silanyloxy)-6-trimethylsilanylethynyl-5,6-dihydro-2H-pyran-2-ylmethyl ester

Base Information

Chemical Name:Acetic acid (2S,5R,6R)-5-(tert-butyl-diphenyl-silanyloxy)-6-trimethylsilanylethynyl-5,6-dihydro-2H-pyran-2-ylmethyl ester
CAS No.:152388-68-6
Molecular Formula:C₂₉H₃₈O₄Si₂
Molecular Weight:506.789
Hs Code.:

Synonyms:Acetic acid (2S,5R,6R)-5-(tert-butyl-diphenyl-silanyloxy)-6-trimethylsilanylethynyl-5,6-dihydro-2H-pyran-2-ylmethyl ester

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Chemical Property of Acetic acid (2S,5R,6R)-5-(tert-butyl-diphenyl-silanyloxy)-6-trimethylsilanylethynyl-5,6-dihydro-2H-pyran-2-ylmethyl ester

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Technology Process of Acetic acid (2S,5R,6R)-5-(tert-butyl-diphenyl-silanyloxy)-6-trimethylsilanylethynyl-5,6-dihydro-2H-pyran-2-ylmethyl ester

There total 2 articles about Acetic acid (2S,5R,6R)-5-(tert-butyl-diphenyl-silanyloxy)-6-trimethylsilanylethynyl-5,6-dihydro-2H-pyran-2-ylmethyl 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: 100.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

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

: 152388-68-6
Acetic acid (2S,5R,6R)-5-(tert-butyl-diphenyl-silanyloxy)-6-trimethylsilanylethynyl-5,6-dihydro-2H-pyran-2-ylmethyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide;
DOI:10.1021/ol0256264

Reference yield:

: 3366-47-0
2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabinohex-1-enopyranose

: 152388-68-6
Acetic acid (2S,5R,6R)-5-(tert-butyl-diphenyl-silanyloxy)-6-trimethylsilanylethynyl-5,6-dihydro-2H-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: SnCl₄ / CH₂Cl₂ / -20 °C

1.2: 86 percent / NaBH₄; CeCl₃ / methanol / 0 °C

2.1: 100 percent / imidazole / dimethylformamide

With 1H-imidazole; tin(IV) chloride; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol0256264

Reference yield:

: 152388-68-6
Acetic acid (2S,5R,6R)-5-(tert-butyl-diphenyl-silanyloxy)-6-trimethylsilanylethynyl-5,6-dihydro-2H-pyran-2-ylmethyl ester

: 419549-17-0
(S)-1-[(2S,3R,6S)-6-Benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-propane-1,3-diol

Guidance literature:: Multi-step reaction with 8 steps

1.1: Co₂(CO)8 / CH₂Cl₂ / 20 °C

1.2: BF₃*Et₂O / CH₂Cl₂ / 0 - 20 °C

1.3: 92 percent / I₂ / tetrahydrofuran

2.1: 99 percent / K₂CO₃ / methanol / 2 h / 20 °C

3.1: 87 percent / KOH / 2 h / 90 °C

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

4.2: 55 percent / tetrahydrofuran; hexane / 17 h / -78 - 0 °C

5.1: 95 percent / Red-Al(R) / tetrahydrofuran; toluene / 0.58 h / 0 - 20 °C

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

7.1: 1.92 g / Red-Al(R) / toluene / 1.5 h / 0 °C

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

With potassium hydroxide; disodium hydrogenphosphate; n-butyllithium; dicobalt octacarbonyl; 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; toluene;
DOI:10.1021/ol0256264