methyl (2Z,5R)-3-(2-benzyloxymethoxyethyl)-6-(4-methoxybenzyloxy)-5-triethylsilyloxyhex-2-enoate

Base Information

Chemical Name:methyl (2Z,5R)-3-(2-benzyloxymethoxyethyl)-6-(4-methoxybenzyloxy)-5-triethylsilyloxyhex-2-enoate
CAS No.:1083348-84-8
Molecular Formula:C₃₁H₄₆O₇Si
Molecular Weight:558.788
Hs Code.:

Synonyms:methyl (2Z,5R)-3-(2-benzyloxymethoxyethyl)-6-(4-methoxybenzyloxy)-5-triethylsilyloxyhex-2-enoate

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Chemical Property of methyl (2Z,5R)-3-(2-benzyloxymethoxyethyl)-6-(4-methoxybenzyloxy)-5-triethylsilyloxyhex-2-enoate

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Technology Process of methyl (2Z,5R)-3-(2-benzyloxymethoxyethyl)-6-(4-methoxybenzyloxy)-5-triethylsilyloxyhex-2-enoate

There total 5 articles about methyl (2Z,5R)-3-(2-benzyloxymethoxyethyl)-6-(4-methoxybenzyloxy)-5-triethylsilyloxyhex-2-enoate 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: 93.0%

: 3587-60-8
Benzyloxymethyl chloride

: 1083349-08-9
methyl (2Z,5R)-3-(2-hydroxyethyl)-6-(4-methoxybenzyloxy)-5-triethylsilyloxyhex-2-enoate

: 1083348-84-8
methyl (2Z,5R)-3-(2-benzyloxymethoxyethyl)-6-(4-methoxybenzyloxy)-5-triethylsilyloxyhex-2-enoate

Guidance literature:: With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 ℃; for 16h;
DOI:10.1016/j.tetlet.2008.08.075

Reference yield:

: 807363-99-1
methyl (2Z,5R)-5-hydroxy-6-(4-methoxybenzyloxy)-3-prop-2-enylhex-2-enoate

: 1083348-84-8
methyl (2Z,5R)-3-(2-benzyloxymethoxyethyl)-6-(4-methoxybenzyloxy)-5-triethylsilyloxyhex-2-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1H-imidazole / dichloromethane / 2 h / 20 °C

2.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone; tert-butyl alcohol / 4 h / 20 °C

3.1: sodium periodate / methanol; tetrahydrofuran / 0 °C

3.2: 1 h / Cooling

4.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C

With 1H-imidazole; sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetone; tert-butyl alcohol;
DOI:10.1039/c7ob02127e

Reference yield:

: 1083349-07-8
methyl (2Z,5RS)-3-[(2R)-3-(4-methoxybenzyloxy)-2-triethylsilyloxypropyl]-5,6-dihydroxyhex-2-enoate

: 1083348-84-8
methyl (2Z,5R)-3-(2-benzyloxymethoxyethyl)-6-(4-methoxybenzyloxy)-5-triethylsilyloxyhex-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium periodate / methanol; tetrahydrofuran / 0 °C

1.2: 1 h / Cooling

2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C

With sodium periodate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol;
DOI:10.1039/c7ob02127e