(2R,2'S,4'S,5R,5'R)-4'-(dimethylphenylsilanyl)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-5'-[(1S)-1-(tert-butyldimethylsilanyloxy)undecyl]octahydro-2,2'-bifuran

Base Information

Chemical Name:(2R,2'S,4'S,5R,5'R)-4'-(dimethylphenylsilanyl)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-5'-[(1S)-1-(tert-butyldimethylsilanyloxy)undecyl]octahydro-2,2'-bifuran
CAS No.:867357-72-0
Molecular Formula:C₅₀H₉₆O₄Si₃
Molecular Weight:845.566
Hs Code.:

(2R,2'S,4'S,5R,5'R)-4'-(dimethylphenylsilanyl)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-5'-[(1S)-1-(tert-butyldimethylsilanyloxy)undecyl]octahydro-2,2'-bifuran

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Chemical Property of (2R,2'S,4'S,5R,5'R)-4'-(dimethylphenylsilanyl)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-5'-[(1S)-1-(tert-butyldimethylsilanyloxy)undecyl]octahydro-2,2'-bifuran

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Technology Process of (2R,2'S,4'S,5R,5'R)-4'-(dimethylphenylsilanyl)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-5'-[(1S)-1-(tert-butyldimethylsilanyloxy)undecyl]octahydro-2,2'-bifuran

There total 7 articles about (2R,2'S,4'S,5R,5'R)-4'-(dimethylphenylsilanyl)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-5'-[(1S)-1-(tert-butyldimethylsilanyloxy)undecyl]octahydro-2,2'-bifuran 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:

: 867357-63-9
(2R,5S)-5-(benzyloxymethyl)-2-[(1R)-1-(hydroxy)undecyl]tetrahydrofuran

: 867357-72-0
(2R,2'S,4'S,5R,5'R)-4'-(dimethylphenylsilanyl)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-5'-[(1S)-1-(tert-butyldimethylsilanyloxy)undecyl]octahydro-2,2'-bifuran

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / imidazole / dimethylformamide / 24 h / 20 °C

2.1: 96 percent / H₂ / Pd(OH)2/C / tetrahydrofuran / 2 h / 20 °C

3.1: 100 percent / (i-Pr)2NEt; DMSO; SO₃*pyridine / CH₂Cl₂ / 0.67 h / 0 °C

4.1: BF₃*Et₂O / tetrahydrofuran; hexane / 4 h / -78 °C

4.2: imidazole / dimethylformamide / 72 h / 20 °C

4.3: 62 mg / BF₃*Et₂O / CH₂Cl₂ / 7 h / -78 °C

With 1H-imidazole; pyridine-SO₃ complex; boron trifluoride diethyl etherate; hydrogen; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo0511290

Reference yield:

: 867357-64-0
(2R,5S)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]tetrahydrofuran

: 867357-72-0
(2R,2'S,4'S,5R,5'R)-4'-(dimethylphenylsilanyl)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-5'-[(1S)-1-(tert-butyldimethylsilanyloxy)undecyl]octahydro-2,2'-bifuran

Guidance literature:: Multi-step reaction with 3 steps

1.1: 96 percent / H₂ / Pd(OH)2/C / tetrahydrofuran / 2 h / 20 °C

2.1: 100 percent / (i-Pr)2NEt; DMSO; SO₃*pyridine / CH₂Cl₂ / 0.67 h / 0 °C

3.1: BF₃*Et₂O / tetrahydrofuran; hexane / 4 h / -78 °C

3.2: imidazole / dimethylformamide / 72 h / 20 °C

3.3: 62 mg / BF₃*Et₂O / CH₂Cl₂ / 7 h / -78 °C

With pyridine-SO₃ complex; boron trifluoride diethyl etherate; hydrogen; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo0511290

Reference yield:

: 112-44-7
undecylaldehyde

: 867357-72-0
(2R,2'S,4'S,5R,5'R)-4'-(dimethylphenylsilanyl)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-5'-[(1S)-1-(tert-butyldimethylsilanyloxy)undecyl]octahydro-2,2'-bifuran

Guidance literature:: Multi-step reaction with 5 steps

1.1: 100 percent / imidazole / dimethylformamide / 24 h / 20 °C

2.1: 96 percent / H₂ / Pd(OH)2/C / tetrahydrofuran / 2 h / 20 °C

3.1: 100 percent / (i-Pr)2NEt; DMSO; SO₃*pyridine / CH₂Cl₂ / 0.67 h / 0 °C

4.1: BF₃*Et₂O / tetrahydrofuran; hexane / 4 h / -78 °C

4.2: imidazole / dimethylformamide / 72 h / 20 °C

4.3: 62 mg / BF₃*Et₂O / CH₂Cl₂ / 7 h / -78 °C

With 1H-imidazole; pyridine-SO₃ complex; boron trifluoride diethyl etherate; hydrogen; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo0511290