1-{(Z)-6-[(1R,2R,3R,5S)-2-[(R)-3-(triethylsilyloxy)-5-phenylpentyl]-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-[(R)-3-(triethylsilyloxy)-5-phenylpentyl]-3,5-bis(triethylsilyloxy)cyclopentyl]hex-4-enyl}-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane
• CAS No.: 913258-28-3
• Molecular Formula: C₄₆H₈₄O₆Si₃
• Molecular Weight: 817.426
• Mol file: 913258-28-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{(Z)-6-[(1R,2R,3R,5S)-2-[(R)-3-(triethylsilyloxy)-5-phenylpentyl]-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-[(R)-3-(triethylsilyloxy)-5-phenylpentyl]-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: 99.0%

1-{(Z)-6-[(1R,2R,3R,5S)-2-[(3S)-3-(triethylsilyloxy)-5-phenyl-1-(phenylsulfonyl)pentyl]-3,5-bis(triethylsilyloxy)cyclopentyl]hex-4-enyl}-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane → 1-{(Z)-6-[(1R,2R,3R,5S)-2-[(R)-3-(triethylsilyloxy)-5-phenylpentyl]-3,5-bis(triethylsilyloxy)cyclopentyl]hex-4-enyl}-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (913258-28-3)

Guidance literature:

With disodium hydrogenphosphate; sodium amalgam; In methanol; at 0 - 20 ℃;

DOI:10.1002/ejoc.200600749

Reference yield: 69.6%

1-{(Z)-6-[(1R,2R,3R,5S)-2-[(3S)-3-(triethylsilyloxy)-5-phenyl-1-(phenylsulfonyl)pentyl]-3,5-bis(triethylsilyloxy)cyclopentyl]hex-4-enyl}-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane → 1-{(Z)-6-[(1R,2R,3R,5S)-2-[(R)-3-(triethylsilyloxy)-5-phenylpentyl]-3,5-bis(triethylsilyloxy)cyclopentyl]hex-4-enyl}-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (913258-28-3) + 2,2-bis(hydroxymethyl)propyl (Z)-7-[(1R,2R,3R,5S)-2-((R)-3-triethylsilyloxy-5-phenylpentyl)-3,5-bis-(triethylsilyloxy)cyclopentyl]hept-5-enate

Guidance literature:

With disodium hydrogenphosphate; sodium-mercury amalgam (10%); In methanol; at 0 - 20 ℃; for 1.83333h;

Reference yield:

(S)-4-phenyl-1-iodo-2-(triethylsiloxy)butane (913258-20-5) + 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) → methyl (Z)-7-[(1R,2R,3R,5S)-2-((3S)-3-triethylsilyloxy-5-phenyl-1-(phenylsulfonyl)pentyl)-3,5-bis(triethylsilyloxy)cyclopentyl]hept-5-enoate (930118-48-2) + 1-{(Z)-6-[(1R,2R,3R,5S)-2-[(R)-3-(triethylsilyloxy)-5-phenylpentyl]-3,5-bis(triethylsilyloxy)cyclopentyl]hex-4-enyl}-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (913258-28-3)

Guidance literature:

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; With lithium hexamethyldisilazane; In tetrahydrofuran; at -70 - 0 ℃; for 0.416667h;

(S)-4-phenyl-1-iodo-2-(triethylsiloxy)butane; In tetrahydrofuran; at -60 - 20 ℃; for 20.5h;

With disodium hydrogenphosphate; sodium amalgam; In methanol; at 0 - 12 ℃; for 6h;

DOI:10.1002/ejoc.200600749

upstream raw materials:

(S)-4-phenyl-1-iodo-2-(triethylsiloxy)butane

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

Downstream raw materials:

latanoprost acid

isopropyl (E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate