(4S,5R,6S)-7-(4-methoxybenzyloxy)-5-trimethylsilyloxy-4,6-dimethylhept-2-yne

Base Information

• Chemical Name: (4S,5R,6S)-7-(4-methoxybenzyloxy)-5-trimethylsilyloxy-4,6-dimethylhept-2-yne
• CAS No.: 1185750-45-1
• Molecular Formula: C₂₀H₃₂O₃Si
• Molecular Weight: 348.558

Synonyms:(4S,5R,6S)-7-(4-methoxybenzyloxy)-5-trimethylsilyloxy-4,6-dimethylhept-2-yne

Chemical Property of (4S,5R,6S)-7-(4-methoxybenzyloxy)-5-trimethylsilyloxy-4,6-dimethylhept-2-yne

Chemical Property:

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Technology Process of (4S,5R,6S)-7-(4-methoxybenzyloxy)-5-trimethylsilyloxy-4,6-dimethylhept-2-yne

There total 3 articles about (4S,5R,6S)-7-(4-methoxybenzyloxy)-5-trimethylsilyloxy-4,6-dimethylhept-2-yne 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: 78.0%

chloro-trimethyl-silane (75-77-4) + (2S,3R,4S)-1-(4-methoxybenzyloxy)-2,4-dimethylhept-5-yn-3-ol (1185750-42-8) → (4S,5R,6S)-7-(4-methoxybenzyloxy)-5-trimethylsilyloxy-4,6-dimethylhept-2-yne (1185750-45-1)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2009.04.073

Reference yield:

M-(-)-2-(tributylstannyl)-2,3-pentadiene → (4S,5R,6S)-7-(4-methoxybenzyloxy)-5-trimethylsilyloxy-4,6-dimethylhept-2-yne (1185750-45-1)

Guidance literature:

Multi-step reaction with 2 steps

1: magnesium bromide ethyl etherate / dichloromethane / 18 h / -23 °C / Inert atmosphere

2: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere

With magnesium bromide ethyl etherate; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2009.04.073

Reference yield:

(2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal (132969-60-9) → (4S,5R,6S)-7-(4-methoxybenzyloxy)-5-trimethylsilyloxy-4,6-dimethylhept-2-yne (1185750-45-1)

Guidance literature:

Multi-step reaction with 2 steps

1: magnesium bromide ethyl etherate / dichloromethane / 18 h / -23 °C / Inert atmosphere

2: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere

With magnesium bromide ethyl etherate; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2009.04.073

upstream raw materials:

chloro-trimethyl-silane

(2S,3R,4S)-1-(4-methoxybenzyloxy)-2,4-dimethylhept-5-yn-3-ol

(2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal

Downstream raw materials:

(2S,3R,4S,5E,7E)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-1-(4-methoxybenzyloxy)-2,4,6-trimethylocta-5,7-dien-3-ol

(2S,3R,4S,6S)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-1-(4-methoxybenzyloxy)-2,4,6-trimethyloctan-3-ol

(2R,4R,5S,6S)-4-((3S,5S,6R,7S)-6-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-3,5,7-trimethyloctyl)-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane

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