(2R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]tetrahydrofuran

Base Information

Chemical Name:(2R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]tetrahydrofuran
CAS No.:867357-61-7
Molecular Formula:C₂₉H₅₂O₃Si
Molecular Weight:476.816
Hs Code.:

Synonyms:(2R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]tetrahydrofuran

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Chemical Property of (2R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]tetrahydrofuran

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Technology Process of (2R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]tetrahydrofuran

There total 12 articles about (2R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]tetrahydrofuran 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%

: 867357-54-8
(2R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(hydroxy)undecyl]tetrahydrofuran

: 18162-48-6
tert-butyldimethylsilyl chloride

: 867357-61-7
(2R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]tetrahydrofuran

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 24h;
DOI:10.1021/jo0511290

Reference yield:

: 863604-38-0
(2S,3R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-3-(dimethylphenylsilanyl)tetrahydrofuran

: 867357-61-7
(2R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]tetrahydrofuran

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / TBAF / tetrahydrofuran / 48 h / 80 °C

2: 100 percent / imidazole / dimethylformamide / 24 h / 20 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jo0511290

Reference yield:

: 936915-84-3
(2R)-1,2-(cyclohexylidenedioxy)hept-6-en-3-one

: 867357-61-7
(2R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]tetrahydrofuran

Guidance literature:: Multi-step reaction with 11 steps

1: 95 percent / K-Selectride / tetrahydrofuran / -78 °C

2: 96 percent / pyridine / 0 °C

3: 83 percent / ADmix-β / 2-methyl-propan-2-ol; H2O / 0 °C

4: 90 percent / pyridine / 0 °C

5: 92 percent / K₂CO₃ / methanol / 20 °C

6: 90 percent / NaH / tetrahydrofuran / Heating

7: 87 percent / aq. CF₃CO₂H / 0 °C

8: 87 percent / pyridine / 0 °C

9: 86 percent / K₂CO₃ / methanol / 20 °C

10: 84 percent / CuI / tetrahydrofuran / -50 °C

11: 88 percent / imidazole / 20 °C

With pyridine; 1H-imidazole; copper(l) iodide; sodium hydride; potassium tri-sec-butyl-borohydride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; trifluoroacetic acid; In tetrahydrofuran; methanol; water; tert-butyl alcohol; 3: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.tetlet.2007.02.093