ethyl (4S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-4-methylhexanoate

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Chemical Name:ethyl (4S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-4-methylhexanoate
CAS No.:1299293-74-5
Molecular Formula:C₂₃H₄₀O₅Si
Molecular Weight:424.653
Hs Code.:

Synonyms:ethyl (4S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-4-methylhexanoate

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Chemical Property of ethyl (4S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-4-methylhexanoate

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Technology Process of ethyl (4S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-4-methylhexanoate

There total 8 articles about ethyl (4S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-4-methylhexanoate 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: 98.0%

: 1299293-73-4
ethyl (2E,4S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-4-methylhex-2-enoate

: 1299293-74-5
ethyl (4S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-4-methylhexanoate

Guidance literature:: With 10% palladium on activated charcoal; hydrogen; In ethyl acetate; at 20 ℃; for 18h;
DOI:10.1055/s-0030-1259287

Reference yield:

: 1299293-72-3
(4R)-4-benzyl-3-{(2R,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-[(4-methoxybenzyl)oxy]-2-methylbutanoyl}-1,3-oxazolidin-2-one

: 1299293-74-5
ethyl (4S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-4-methylhexanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium borohydride / tetrahydrofuran; methanol / 19 h / 0 - 20 °C

2.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 20 °C

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 1 h / 0 °C

3.2: 0 - 20 °C

4.1: 10% palladium on activated charcoal; hydrogen / ethyl acetate / 18 h / 20 °C

With lithium borohydride; 10% palladium on activated charcoal; hydrogen; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetonitrile; 2.1: Dess-Martin oxidation / 3.1: Wittig-Horner reaction / 3.2: Wittig-Horner reaction;
DOI:10.1055/s-0030-1259287

Reference yield:

: 109786-74-5,109786-77-8,13807-95-9
(±)-3-(4-methoxybenzyloxy)propane-1,2-diol

: 1299293-74-5
ethyl (4S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-4-methylhexanoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium periodate; water / dichloromethane / 0 - 20 °C

2.1: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane / 0 °C

2.2: 1.33 h / -80 - 0 °C

3.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C

4.1: lithium borohydride / tetrahydrofuran; methanol / 19 h / 0 - 20 °C

5.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 20 °C

6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 1 h / 0 °C

6.2: 0 - 20 °C

7.1: 10% palladium on activated charcoal; hydrogen / ethyl acetate / 18 h / 20 °C

With 2,6-dimethylpyridine; sodium periodate; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; 10% palladium on activated charcoal; water; hydrogen; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetonitrile; 5.1: Dess-Martin oxidation / 6.1: Wittig-Horner reaction / 6.2: Wittig-Horner reaction;
DOI:10.1055/s-0030-1259287