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

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Chemical Name:(4S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-4-methylhexanoic acid
CAS No.:1299293-75-6
Molecular Formula:C₂₁H₃₆O₅Si
Molecular Weight:396.599
Hs Code.:

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

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

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

There total 9 articles about (4S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-4-methylhexanoic 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: 98.0%

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

: 1299293-75-6
(4S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-4-methylhexanoic acid

Guidance literature:: With water; sodium hydroxide; In ethanol; at 0 - 20 ℃;
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

: 1299293-75-6
(4S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-4-methylhexanoic acid

Guidance literature:: Multi-step reaction with 5 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

5.1: water; sodium hydroxide / ethanol / 0 - 20 °C

With lithium borohydride; 10% palladium on activated charcoal; water; hydrogen; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; 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

: 1299293-75-6
(4S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-4-methylhexanoic acid

Guidance literature:: Multi-step reaction with 8 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

8.1: water; sodium hydroxide / ethanol / 0 - 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; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; 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