(2R,2'R,4R,4'R,5S,5'S)-4,4'-bis-(dimethylphenylsilanyl)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-5'-[(1R,12R,16R)-1,12-bis-(tert-butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)heptadec-14-yne]octahydro-2,2'-bifuran

Base Information

• Chemical Name: (2R,2'R,4R,4'R,5S,5'S)-4,4'-bis-(dimethylphenylsilanyl)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-5'-[(1R,12R,16R)-1,12-bis-(tert-butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)heptadec-14-yne]octahydro-2,2'-bifuran
• CAS No.: 863604-45-9
• Molecular Formula: C₈₆H₁₄₆O₆Si₆
• Molecular Weight: 1444.61

Synonyms:(2R,2'R,4R,4'R,5S,5'S)-4,4'-bis-(dimethylphenylsilanyl)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-5'-[(1R,12R,16R)-1,12-bis-(tert-butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)heptadec-14-yne]octahydro-2,2'-bifuran

Chemical Property of (2R,2'R,4R,4'R,5S,5'S)-4,4'-bis-(dimethylphenylsilanyl)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-5'-[(1R,12R,16R)-1,12-bis-(tert-butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)heptadec-14-yne]octahydro-2,2'-bifuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,2'R,4R,4'R,5S,5'S)-4,4'-bis-(dimethylphenylsilanyl)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-5'-[(1R,12R,16R)-1,12-bis-(tert-butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)heptadec-14-yne]octahydro-2,2'-bifuran

There total 9 articles about (2R,2'R,4R,4'R,5S,5'S)-4,4'-bis-(dimethylphenylsilanyl)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-5'-[(1R,12R,16R)-1,12-bis-(tert-butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)heptadec-14-yne]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:

(2R,4R,5S)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-carbaldehyde (863604-39-1) + (3S,4R,15R,19R)-4,15-bis(tert-bytyldimethylsilanyloxy)-19-(tert-butyldiphenylsilanyloxy)-3-(dimethylphenylsilanyl)eicos-1-en-17-yne (863604-34-6) → (2R,2'R,4R,4'R,5S,5'S)-4,4'-bis-(dimethylphenylsilanyl)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-5'-[(1R,12R,16R)-1,12-bis-(tert-butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)heptadec-14-yne]octahydro-2,2'-bifuran (863604-45-9)

Guidance literature:

With 4 A molecular sieve; tin(IV) chloride; In dichloromethane; at 0 ℃; for 4h;

DOI:10.1021/ja051986l

Reference yield:

(2R,4R,5S)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-carbaldehyde (863604-39-1) + (3S,4R,15R,19R)-4,15-bis(tert-bytyldimethylsilanyloxy)-19-(tert-butyldiphenylsilanyloxy)-3-(dimethylphenylsilanyl)eicos-1-en-17-yne (863604-34-6) → (E)-(1R,5R,16R,20R)-5,16-Bis-(tert-butyl-dimethyl-silanyloxy)-1-[(2R,4R,5S)-5-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-undecyl]-4-(dimethyl-phenyl-silanyl)-tetrahydro-furan-2-yl]-20-(tert-butyl-diphenyl-silanyloxy)-henicos-3-en-18-yn-1-ol + (2R,2'R,4R,4'R,5S,5'S)-4,4'-bis-(dimethylphenylsilanyl)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-5'-[(1R,12R,16R)-1,12-bis-(tert-butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)heptadec-14-yne]octahydro-2,2'-bifuran (863604-45-9)

Guidance literature:

With 4 A molecular sieve; tin(IV) chloride; In dichloromethane; at -40 ℃;

DOI:10.1021/ja051986l

Reference yield:

(2R,4R,5S)-[5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methanol (863604-46-0) → (2R,2'R,4R,4'R,5S,5'S)-4,4'-bis-(dimethylphenylsilanyl)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-5'-[(1R,12R,16R)-1,12-bis-(tert-butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)heptadec-14-yne]octahydro-2,2'-bifuran (863604-45-9)

Guidance literature:

Multi-step reaction with 2 steps

1: diisopropylethyl amine; DMSO; SO₃*pyridine / CH₂Cl₂ / 1 h / 0 °C

2: 4 Angstroem molecular sieves; SnCl₄ / CH₂Cl₂ / -40 °C

With pyridine-SO₃ complex; 4 A molecular sieve; tin(IV) chloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; 1: Parikh-Doering oxidation;

DOI:10.1021/ja051986l

upstream raw materials:

(2R,4R,5S)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-carbaldehyde

(3S,4R,15R,19R)-4,15-bis(tert-bytyldimethylsilanyloxy)-19-(tert-butyldiphenylsilanyloxy)-3-(dimethylphenylsilanyl)eicos-1-en-17-yne

(2R,4R,5S)-[5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methanol

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

Downstream raw materials:

(+)-asimicin

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