(Z)-(5S,6S,7S,8R)-11-iodo-8-(4-methoxybenzyloxy)-5,7-dimethylundeca-1,3-dien-6-yl tert-butyldimethylsilyl ether

Base Information

• Chemical Name: (Z)-(5S,6S,7S,8R)-11-iodo-8-(4-methoxybenzyloxy)-5,7-dimethylundeca-1,3-dien-6-yl tert-butyldimethylsilyl ether
• CAS No.: 623926-35-2
• Molecular Formula: C₂₇H₄₅IO₃Si
• Molecular Weight: 572.643
• Mol file: 623926-35-2.mol

Synonyms:(Z)-(5S,6S,7S,8R)-11-iodo-8-(4-methoxybenzyloxy)-5,7-dimethylundeca-1,3-dien-6-yl tert-butyldimethylsilyl ether

Chemical Property of (Z)-(5S,6S,7S,8R)-11-iodo-8-(4-methoxybenzyloxy)-5,7-dimethylundeca-1,3-dien-6-yl tert-butyldimethylsilyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(5S,6S,7S,8R)-11-iodo-8-(4-methoxybenzyloxy)-5,7-dimethylundeca-1,3-dien-6-yl tert-butyldimethylsilyl ether

There total 14 articles about (Z)-(5S,6S,7S,8R)-11-iodo-8-(4-methoxybenzyloxy)-5,7-dimethylundeca-1,3-dien-6-yl tert-butyldimethylsilyl ether 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: 89.0%

(Z)-(4R,5S,6S,7S)-6-(tert-butyldimethylsilanyloxy)-4-(4-methoxybenzyloxy)-5,7-dimethylundeca-8,10-dien-1-ol (479673-43-3) → (Z)-(5S,6S,7S,8R)-11-iodo-8-(4-methoxybenzyloxy)-5,7-dimethylundeca-1,3-dien-6-yl tert-butyldimethylsilyl ether (623926-35-2)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In diethyl ether; benzene; at 20 ℃; for 1h;

DOI:10.1016/S0968-0896(03)00186-X

Reference yield:

(2R,3S,4R,5R)-3,8-bis(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2,4-dimethyloctanal (565229-70-1) → (Z)-(5S,6S,7S,8R)-11-iodo-8-(4-methoxybenzyloxy)-5,7-dimethylundeca-1,3-dien-6-yl tert-butyldimethylsilyl ether (623926-35-2)

Guidance literature:

Multi-step reaction with 4 steps

1: CrCl₂ / tetrahydrofuran / 16 h / 20 °C

2: NaH / tetrahydrofuran / 0 - 20 °C

3: 85 percent / HF-pyridine; pyridine / tetrahydrofuran / 12 h / 20 °C

4: 89 percent / PPh₃; imidazole; iodine / benzene; diethyl ether / 1 h / 20 °C

With pyridine; 1H-imidazole; chromium dichloride; iodine; sodium hydride; pyridine hydrogenfluoride; triphenylphosphine; In tetrahydrofuran; diethyl ether; benzene; 1: Nozaki-Hiyama reaction;

DOI:10.1016/S0968-0896(03)00186-X

Reference yield:

(1R,2R,3S,4S,5Z)-1-{3-(tert-butyldimethylsilanyloxy)-1-[3-(tert-butyldimethylsilanyloxy)propyl]-2,4-dimethylocta-5,7-dienyloxymethyl}-4-methoxybenzene (479673-25-1) → (Z)-(5S,6S,7S,8R)-11-iodo-8-(4-methoxybenzyloxy)-5,7-dimethylundeca-1,3-dien-6-yl tert-butyldimethylsilyl ether (623926-35-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / HF-pyridine; pyridine / tetrahydrofuran / 12 h / 20 °C

2: 89 percent / PPh₃; imidazole; iodine / benzene; diethyl ether / 1 h / 20 °C

With pyridine; 1H-imidazole; iodine; pyridine hydrogenfluoride; triphenylphosphine; In tetrahydrofuran; diethyl ether; benzene;

DOI:10.1016/S0968-0896(03)00186-X

upstream raw materials:

(Z)-(4R,5S,6S,7S)-6-(tert-butyldimethylsilanyloxy)-4-(4-methoxybenzyloxy)-5,7-dimethylundeca-8,10-dien-1-ol

(2R,3S,4R,5R)-3,8-bis(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2,4-dimethyloctanal

(1R,2R,3S,4S,5Z)-1-{3-(tert-butyldimethylsilanyloxy)-1-[3-(tert-butyldimethylsilanyloxy)propyl]-2,4-dimethylocta-5,7-dienyloxymethyl}-4-methoxybenzene

(4R,5S,6S,7S)-1,6-bis(tert-butyldimethylsilanyloxy)-5,7-dimethylnon-8-en-4-ol

Downstream raw materials:

(Z,Z,Z)-(6S,7S,8S,13R,14S,15S,16S)-15-(tert-butyldimethylsilanyloxy)-7,13-bis(4-methoxybenzyloxy)-6,8,14,16-tetramethyleicosa-4,9,17,19-tetraen-1-yl tetrahydropyran-2-yl ether

(4-methoxybenzyloxy)acetic acid (Z,Z,Z)-(6S,7S,8S,13R,14S,15S,16S)-15-carbamoyloxy-7,13-bis(4-methoxybenzyloxy)-6,8,14,16-tetramethyleicosa-4,9,17,19-tetraenyl ester

Carbamic acid (6Z,11Z)-(1S,2S,3R,8S,9R,10S)-14-((2S,3S,4S,5R)-4-hydroxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-3,9-bis-(4-methoxy-benzyloxy)-2,8,10-trimethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester

carbamic acid, (1S,2S,3R,6Z,8S,9S,10S,11Z)-3,9-bis(4-methoxybenzyloxy)-14-[(2S,3S,4S,5R)-4-methoxymethoxy-3,5-dimethyl-6-oxotetrahydropyran-2-yl]-2,8,10-trimethyl-1-[(1S,2Z)-1-methylpenta-2,4-dienyl]tetradeca-6,11-dienyl ester