(4S,2'S,3'R)-3-[3'-((4''-toluenesulfonyl)oxy)-2'-methylhexanoyl]-4-isopropyl-2-oxazolidinone

Base Information

Chemical Name:(4S,2'S,3'R)-3-[3'-((4''-toluenesulfonyl)oxy)-2'-methylhexanoyl]-4-isopropyl-2-oxazolidinone
CAS No.:410087-00-2
Molecular Formula:C₂₀H₂₉NO₆S
Molecular Weight:411.519
Hs Code.:

Synonyms:(4S,2'S,3'R)-3-[3'-((4''-toluenesulfonyl)oxy)-2'-methylhexanoyl]-4-isopropyl-2-oxazolidinone

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Chemical Property of (4S,2'S,3'R)-3-[3'-((4''-toluenesulfonyl)oxy)-2'-methylhexanoyl]-4-isopropyl-2-oxazolidinone

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Technology Process of (4S,2'S,3'R)-3-[3'-((4''-toluenesulfonyl)oxy)-2'-methylhexanoyl]-4-isopropyl-2-oxazolidinone

There total 2 articles about (4S,2'S,3'R)-3-[3'-((4''-toluenesulfonyl)oxy)-2'-methylhexanoyl]-4-isopropyl-2-oxazolidinone 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: 70.0%

: 98-59-9
p-toluenesulfonyl chloride

: 410086-99-6
(4S,2'S,3'R)-3-(3'-hydroxy-2'-methylhexanoyl)-4-isopropyl-2-oxazolidinone

: 410087-00-2
(4S,2'S,3'R)-3-[3'-((4''-toluenesulfonyl)oxy)-2'-methylhexanoyl]-4-isopropyl-2-oxazolidinone

Guidance literature:: With pyridine; at 20 ℃; for 70h;
DOI:10.1021/jo010176z

Reference yield:

: 77877-19-1,165657-81-8
N-isopropyl oxazolidinone

: 410087-00-2
(4S,2'S,3'R)-3-[3'-((4''-toluenesulfonyl)oxy)-2'-methylhexanoyl]-4-isopropyl-2-oxazolidinone

Guidance literature:: Multi-step reaction with 2 steps

1.1: dibutylboron triflate; diisopropylethylamine / CH₂Cl₂ / 0.5 h / 0 °C

1.2: 84 percent / CH₂Cl₂ / 2 h / -78 - 20 °C

2.1: 70 percent / pyridine / 70 h / 20 °C

With pyridine; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1021/jo010176z

Reference yield:

: 410087-00-2
(4S,2'S,3'R)-3-[3'-((4''-toluenesulfonyl)oxy)-2'-methylhexanoyl]-4-isopropyl-2-oxazolidinone

: 1181218-07-4
(2S,3R)-methyl 3-(((benzyloxy)carbonyl)amino)-2-methylhexanoate

Guidance literature:: Multi-step reaction with 6 steps

1: lithium bromide / acetone

2: sodium azide; 15-crown-5 / N,N-dimethyl-formamide / 70 °C

3: lithium hydroxide monohydrate; dihydrogen peroxide / tetrahydrofuran; water

4: hydrogen / methanol / 4 h

5: thionyl chloride / 16 h / 0 °C / Reflux

6: sodium hydrogencarbonate / ethyl acetate / 12 h

With thionyl chloride; sodium azide; 15-crown-5; lithium hydroxide monohydrate; hydrogen; dihydrogen peroxide; sodium hydrogencarbonate; lithium bromide; In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja904504j