(2S,3R)-2-((R,E)-6-(tert-butyldimethylsilyloxy)-1-(4-methoxybenzyloxy)hex-4-en-2-yl)-3,7-dimethyloct-6-enoic acid

Base Information

• Chemical Name: (2S,3R)-2-((R,E)-6-(tert-butyldimethylsilyloxy)-1-(4-methoxybenzyloxy)hex-4-en-2-yl)-3,7-dimethyloct-6-enoic acid
• CAS No.: 1163724-81-9
• Molecular Formula: C₂₉H₄₈O₅Si
• Molecular Weight: 504.783

Synonyms:(2S,3R)-2-((R,E)-6-(tert-butyldimethylsilyloxy)-1-(4-methoxybenzyloxy)hex-4-en-2-yl)-3,7-dimethyloct-6-enoic acid

Chemical Property of (2S,3R)-2-((R,E)-6-(tert-butyldimethylsilyloxy)-1-(4-methoxybenzyloxy)hex-4-en-2-yl)-3,7-dimethyloct-6-enoic acid

Chemical Property:

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Technology Process of (2S,3R)-2-((R,E)-6-(tert-butyldimethylsilyloxy)-1-(4-methoxybenzyloxy)hex-4-en-2-yl)-3,7-dimethyloct-6-enoic acid

There total 2 articles about (2S,3R)-2-((R,E)-6-(tert-butyldimethylsilyloxy)-1-(4-methoxybenzyloxy)hex-4-en-2-yl)-3,7-dimethyloct-6-enoic acid 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: 85.0%

chloro-trimethyl-silane (75-77-4) + (R)-((S,Z)-1-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)pent-3-en-2-yl) 3,7-dimethyloct-6-enoate (1163724-80-8) → C29H48O5Si + (2S,3R)-2-((R,E)-6-(tert-butyldimethylsilyloxy)-1-(4-methoxybenzyloxy)hex-4-en-2-yl)-3,7-dimethyloct-6-enoic acid (1163724-81-9)

Guidance literature:

chloro-trimethyl-silane; (R)-((S,Z)-1-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)pent-3-en-2-yl) 3,7-dimethyloct-6-enoate; With triethylamine; lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃; for 3.5h; Inert atmosphere;

In tetrahydrofuran; for 2h; optical yield given as %de; Reflux; Inert atmosphere;

DOI:10.1021/ja902677t

Reference yield:

C32H56O5Si2 → C29H48O5Si + (2S,3R)-2-((R,E)-6-(tert-butyldimethylsilyloxy)-1-(4-methoxybenzyloxy)hex-4-en-2-yl)-3,7-dimethyloct-6-enoic acid (1163724-81-9)

Guidance literature:

In tetrahydrofuran; for 2h; optical yield given as %de; Inert atmosphere; Reflux;

DOI:10.1021/ja902677t

Reference yield: 97.0%

(2S,3R)-2-((R,E)-6-(tert-butyldimethylsilyloxy)-1-(4-methoxybenzyloxy)hex-4-en-2-yl)-3,7-dimethyloct-6-enoic acid (1163724-81-9) + methyl iodide (74-88-4) → methyl (2S,3R)-2-((R,E)-6-(tert-butyldimethylsilyloxy)-1-(4-methoxybenzyloxy)hex-4-en-2-yl)-3,7-dimethyloct-6-enoate (1163725-07-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ja902677t

upstream raw materials:

chloro-trimethyl-silane

(R)-((S,Z)-1-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)pent-3-en-2-yl) 3,7-dimethyloct-6-enoate

Downstream raw materials:

methyl (2S,3R)-2-((R,E)-6-(tert-butyldimethylsilyloxy)-1-(4-methoxybenzyloxy)hex-4-en-2-yl)-3,7-dimethyloct-6-enoate

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