(2R,3S,4S)-2-hydroxy-4-methyl-3-phenylsulfanylcarbonylhexanoic acid ethyl ester

Base Information

Chemical Name:(2R,3S,4S)-2-hydroxy-4-methyl-3-phenylsulfanylcarbonylhexanoic acid ethyl ester
CAS No.:725240-15-3
Molecular Formula:C₁₆H₂₂O₄S
Molecular Weight:310.414
Hs Code.:

Synonyms:(2R,3S,4S)-2-hydroxy-4-methyl-3-phenylsulfanylcarbonylhexanoic acid ethyl ester

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Chemical Property of (2R,3S,4S)-2-hydroxy-4-methyl-3-phenylsulfanylcarbonylhexanoic acid ethyl ester

Chemical Property:

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Technology Process of (2R,3S,4S)-2-hydroxy-4-methyl-3-phenylsulfanylcarbonylhexanoic acid ethyl ester

There total 4 articles about (2R,3S,4S)-2-hydroxy-4-methyl-3-phenylsulfanylcarbonylhexanoic acid ethyl ester 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:

: 924-44-7
glyoxylic acid ethyl ester

: 725240-14-2
trimethyl-[(3S)-methyl-1-phenylsulfanylpent-(1Z)-enyloxy]silane

: 2-hydroxy-4-methyl-3-phenylsulfanylcarbonylhexanoic acid ethyl ester

: 725240-15-3
(2R,3S,4S)-2-hydroxy-4-methyl-3-phenylsulfanylcarbonylhexanoic acid ethyl ester

Guidance literature:: glyoxylic acid ethyl ester; trimethyl-[(3S)-methyl-1-phenylsulfanylpent-(1Z)-enyloxy]silane; With tin(II) trifluoromethanesulfonate; In dichloromethane; at -78 - 20 ℃;

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 2h; Title compound not separated from byproducts;
DOI:10.1021/ol049409+

Reference yield:

: 1730-92-3
(3S)-methylvaleric acid

: 725240-15-3
(2R,3S,4S)-2-hydroxy-4-methyl-3-phenylsulfanylcarbonylhexanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 97 percent / DCC; DMAP / CH₂Cl₂ / 1 h / Heating

2.1: 92 percent / n-BuLi; HTMP / tetrahydrofuran / -78 - 20 °C

3.1: Sn(OTf)2; BOX / CH₂Cl₂ / -78 - 20 °C

3.2: aq. HCl / tetrahydrofuran / 2 h / 20 °C

With 2,2,6,6-tetramethyl-piperidine; dmap; tin(II) trifluoromethanesulfonate; n-butyllithium; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol049409+

Reference yield:

: 73-32-5,959215-79-3,18875-42-8
L-isoleucine

: 725240-15-3
(2R,3S,4S)-2-hydroxy-4-methyl-3-phenylsulfanylcarbonylhexanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 84 percent / hydroxylamine-O-sulfonic acid; aq. NaOH / 27 h / 20 - 100 °C

2.1: 97 percent / DCC; DMAP / CH₂Cl₂ / 1 h / Heating

3.1: 92 percent / n-BuLi; HTMP / tetrahydrofuran / -78 - 20 °C

4.1: Sn(OTf)2; BOX / CH₂Cl₂ / -78 - 20 °C

4.2: aq. HCl / tetrahydrofuran / 2 h / 20 °C

With 2,2,6,6-tetramethyl-piperidine; dmap; sodium hydroxide; tin(II) trifluoromethanesulfonate; n-butyllithium; dicyclohexyl-carbodiimide; hydroxylamine-O-sulfonic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol049409+