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

Base Information

Chemical Name:methyl (2Z,5R)-3-(2-hydroxyethyl)-6-(4-methoxybenzyloxy)-5-triethylsilyloxyhex-2-enoate
CAS No.:1083349-08-9
Molecular Formula:C₂₃H₃₈O₆Si
Molecular Weight:438.637
Hs Code.:

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

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

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

There total 4 articles about methyl (2Z,5R)-3-(2-hydroxyethyl)-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: 76.0%

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

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

Guidance literature:: methyl (2Z,5RS)-3-[(2R)-3-(4-methoxybenzyloxy)-2-triethylsilyloxypropyl]-5,6-dihydroxyhex-2-enoate; With sodium periodate; In tetrahydrofuran; methanol; water; at 0 ℃; for 1h;

With sodium tetrahydroborate; In tetrahydrofuran; methanol; water; at 0 ℃; for 1h;
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

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

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

: 1083348-83-7
(2Z)-methyl 3-[(2R)-3-(4-methoxybenzyloxy)-2-triethylsilyloxypropyl]hexa-2,5-dienoate

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

Guidance literature:: Multi-step reaction with 2 steps

1.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone; tert-butyl alcohol / 4 h / 20 °C

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

2.2: 1 h / Cooling

With sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; water; acetone; tert-butyl alcohol;
DOI:10.1039/c7ob02127e