1-{(Z)-6-[(1R,2R,3R,5S)-2-((Phenylsulfonyl)methyl)-3,5-bis-(triethylsilyloxy)cyclopentyl]hex-4-enyl}-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane

Base Information

• Chemical Name: 1-{(Z)-6-[(1R,2R,3R,5S)-2-((Phenylsulfonyl)methyl)-3,5-bis-(triethylsilyloxy)cyclopentyl]hex-4-enyl}-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane
• CAS No.: 913258-17-0
• Molecular Formula: C₃₆H₆₂O₇SSi₂
• Molecular Weight: 695.121
• DSSTox Substance ID: DTXSID601100542
• Nikkaji Number: J2.421.734E
• Mol file: 913258-17-0.mol

Synonyms:913258-17-0;2,6,7-Trioxabicyclo[2.2.2]octane, 4-methyl-1-[(4Z)-6-[(1R,2R,3R,5S)-2-[(phenylsulfonyl)methyl]-3,5-bis[(triethylsilyl)oxy]cyclopentyl]-4-hexen-1-yl]-;SCHEMBL2076102;FXUAOCJGSHZLLB-BYUORFCVSA-N;DTXSID601100542;1-{(Z)-6-[(1R,2R,3R,5S)-2-((Phenylsulfonyl)methyl)-3,5-bis-(triethylsilyloxy)cyclopentyl]hex-4-enyl}-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane;4-Methyl-1-[(4Z)-6-[(1R,2R,3R,5S)-2-[(phenylsulfonyl)methyl]-3,5-bis[(triethylsilyl)oxy]cyclopentyl]-4-hexen-1-yl]-2,6,7-trioxabicyclo[2.2.2]octane

Chemical Property of 1-{(Z)-6-[(1R,2R,3R,5S)-2-((Phenylsulfonyl)methyl)-3,5-bis-(triethylsilyloxy)cyclopentyl]hex-4-enyl}-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 19
• Exact Mass: 694.37547855
• Heavy Atom Count: 46
• Complexity: 1020

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC[Si](CC)(CC)OC1CC(C(C1CC=CCCCC23OCC(CO2)(CO3)C)CS(=O)(=O)C4=CC=CC=C4)O[Si](CC)(CC)CC
• Isomeric SMILES: CC[Si](CC)(CC)O[C@H]1C[C@H]([C@@H]([C@H]1C/C=C\CCCC23OCC(CO2)(CO3)C)CS(=O)(=O)C4=CC=CC=C4)O[Si](CC)(CC)CC

Technology Process of 1-{(Z)-6-[(1R,2R,3R,5S)-2-((Phenylsulfonyl)methyl)-3,5-bis-(triethylsilyloxy)cyclopentyl]hex-4-enyl}-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane

There total 3 articles about 1-{(Z)-6-[(1R,2R,3R,5S)-2-((Phenylsulfonyl)methyl)-3,5-bis-(triethylsilyloxy)cyclopentyl]hex-4-enyl}-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane 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: 87.0%

(1R,3S,4R,5R)-4-[(Z)-6-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)hex-2-enyl]-5-[(phenylsulfonyl)methyl]cyclopentan-1,3-diol (913258-13-6) + triethylsilyl chloride (994-30-9) → 1-<(Z)-6-{(1R,2R,3R,5S)-2-[(phenylsulfonyl)methyl]-3,5-bis(triethylsiloxy)cyclopentyl}hex-4-enyl>-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (913258-17-0)

Guidance literature:

With 1H-imidazole; triethylamine; In N,N-dimethyl-formamide; at 0 ℃; for 2.5h;

DOI:10.1002/ejoc.200600749

Reference yield: 66.5%

(1R,3S,4R,5R)-4-[(Z)-6-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)hex-2-enyl]-5-[(phenylsulfonyl)methyl]cyclopentan-1,3-diol (913258-13-6) + (1S,2R,3R,4R)-2-[(Z)-6-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)hex-2-enyl]-3-[(phenylsulfonyl)methyl]-4-(triethylsilyloxy)cyclopentanol (913258-15-8) + (1R,2R,3R,4S)-3-[(Z)-6-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)hex-2-enyl]-2-[(phenylsulfonyl)methyl]-4-(triethylsilyloxy)cyclopentanol (913258-14-7) + triethylsilyl chloride (994-30-9) → 1-<(Z)-6-{(1R,2R,3R,5S)-2-[(phenylsulfonyl)methyl]-3,5-bis(triethylsiloxy)cyclopentyl}hex-4-enyl>-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (913258-17-0) + (Z)-7-[(1R,2R,3R,5S)-2-((phenylsulfonyl)methyl)-3,5-bis-(triethylsilyloxy)cyclopentyl]hept-5-enoic acid 2,2-bis(hydroxymethyl)propyl ester (913258-18-1)

Guidance literature:

With 1H-imidazole; triethylamine; In N,N-dimethyl-formamide; at 0 - 4 ℃;

Reference yield: 53.0%

(3aR,4R,5R,6aS)-4-[(phenylsulfonyl)methyl]-5-(triethylsilyloxy)-hexahydro-cyclopenta[b]furan-2-ol (913258-10-3) + [4-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-y)butyl]triphenylphosphonium iodide + triethylsilyl chloride (994-30-9) → 1-<(Z)-6-{(1R,2R,3R,5S)-2-[(phenylsulfonyl)methyl]-3,5-bis(triethylsiloxy)cyclopentyl}hex-4-enyl>-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (913258-17-0)

Guidance literature:

[4-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-y)butyl]triphenylphosphonium iodide; With potassium tert-butylate; In tetrahydrofuran; at 6 - 20 ℃; for 0.666667h;

(3aR,4R,5R,6aS)-4-[(phenylsulfonyl)methyl]-5-(triethylsilyloxy)-hexahydro-cyclopenta[b]furan-2-ol; With aluminum tri-tert-butoxide; In tetrahydrofuran; at 2 - 20 ℃; for 19.5h;

triethylsilyl chloride; With 1H-imidazole; triethylamine; In tetrahydrofuran; at 0 - 5 ℃; for 1h;

DOI:10.1002/ejoc.200600749

upstream raw materials:

(3aR,4R,5R,6aS)-4-[(phenylsulfonyl)methyl]-5-(triethylsilyloxy)-hexahydro-cyclopenta[b]furan-2-ol

triethylsilyl chloride

(1R,3S,4R,5R)-4-[(Z)-6-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)hex-2-enyl]-5-[(phenylsulfonyl)methyl]cyclopentan-1,3-diol

(1S,2R,3R,4R)-2-[(Z)-6-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)hex-2-enyl]-3-[(phenylsulfonyl)methyl]-4-(triethylsilyloxy)cyclopentanol

Downstream raw materials:

(5Z)-N-ethyl-7-{(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-(phnoxy)but-1-enyl]-3,5-dihydroxycyclopentyl}hept-5-enamide

tafluprost

AFP-172

(1R,2R,3R,4S)-3-[(Z)-6-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)hex-2-enyl]-2-[(phenylsulfonyl)methyl]-4-(triethylsilyloxy)cyclopentanol