(4R,5S)-4-[(R)-1-Hydroxy-1-((R)-3-oxo-1,4-dioxa-spiro[4.5]dec-2-yl)-ethyl]-2,2,5-trimethyl-oxazolidine-3-carboxylic acid benzyl ester

Base Information

Chemical Name:(4R,5S)-4-[(R)-1-Hydroxy-1-((R)-3-oxo-1,4-dioxa-spiro[4.5]dec-2-yl)-ethyl]-2,2,5-trimethyl-oxazolidine-3-carboxylic acid benzyl ester
CAS No.:374073-08-2
Molecular Formula:C₂₄H₃₃NO₇
Molecular Weight:447.529
Hs Code.:

Synonyms:(4R,5S)-4-[(R)-1-Hydroxy-1-((R)-3-oxo-1,4-dioxa-spiro[4.5]dec-2-yl)-ethyl]-2,2,5-trimethyl-oxazolidine-3-carboxylic acid benzyl ester

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Chemical Property of (4R,5S)-4-[(R)-1-Hydroxy-1-((R)-3-oxo-1,4-dioxa-spiro[4.5]dec-2-yl)-ethyl]-2,2,5-trimethyl-oxazolidine-3-carboxylic acid benzyl ester

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Technology Process of (4R,5S)-4-[(R)-1-Hydroxy-1-((R)-3-oxo-1,4-dioxa-spiro[4.5]dec-2-yl)-ethyl]-2,2,5-trimethyl-oxazolidine-3-carboxylic acid benzyl ester

There total 6 articles about (4R,5S)-4-[(R)-1-Hydroxy-1-((R)-3-oxo-1,4-dioxa-spiro[4.5]dec-2-yl)-ethyl]-2,2,5-trimethyl-oxazolidine-3-carboxylic acid benzyl 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: 80.0%

: 4423-79-4
cyclohexanespiro-2'-(1',3'-dioxolan)-4'-one

: 374072-95-4
phenylmethyl-(5S,4R)-4-acetyl-2,2,5-trimethyl-1,3-oxazolidine-3-carboxylate

: 374073-08-2
(4R,5S)-4-[(R)-1-Hydroxy-1-((R)-3-oxo-1,4-dioxa-spiro[4.5]dec-2-yl)-ethyl]-2,2,5-trimethyl-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:: cyclohexanespiro-2'-(1',3'-dioxolan)-4'-one; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -50 ℃; for 0.25h;

phenylmethyl-(5S,4R)-4-acetyl-2,2,5-trimethyl-1,3-oxazolidine-3-carboxylate; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Further stages.;
DOI:10.1021/ol016416e

Reference yield:

: 84449-06-9
methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate

: 374073-08-2
(4R,5S)-4-[(R)-1-Hydroxy-1-((R)-3-oxo-1,4-dioxa-spiro[4.5]dec-2-yl)-ethyl]-2,2,5-trimethyl-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 11.96 g / toluenesulfonic acid monohydrate / benzene / 12 h / 20 °C

2.1: isopropylmagnesium chloride / tetrahydrofuran / 0.08 h / -78 °C

2.2: 93 percent / tetrahydrofuran / -78 - -40 °C

3.1: 69 percent / tetrahydrofuran; diethyl ether / -40 - 20 °C

4.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 0.25 h / -50 °C

4.2: 80 percent / tetrahydrofuran; hexane / 2 h / -78 °C

With n-butyllithium; isopropylmagnesium chloride; toluene-4-sulfonic acid; diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; benzene;
DOI:10.1021/ol016416e

Reference yield:

: 5618-95-1,19728-63-3,41151-16-0,85995-53-5,119221-16-8,80384-27-6
(2R,3S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxybutanoic acid

: 374073-08-2
(4R,5S)-4-[(R)-1-Hydroxy-1-((R)-3-oxo-1,4-dioxa-spiro[4.5]dec-2-yl)-ethyl]-2,2,5-trimethyl-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: K₂CO₃ / dimethylformamide / 0 - 20 °C

2.1: 11.96 g / toluenesulfonic acid monohydrate / benzene / 12 h / 20 °C

3.1: isopropylmagnesium chloride / tetrahydrofuran / 0.08 h / -78 °C

3.2: 93 percent / tetrahydrofuran / -78 - -40 °C

4.1: 69 percent / tetrahydrofuran; diethyl ether / -40 - 20 °C

5.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 0.25 h / -50 °C

5.2: 80 percent / tetrahydrofuran; hexane / 2 h / -78 °C

With n-butyllithium; isopropylmagnesium chloride; potassium carbonate; toluene-4-sulfonic acid; diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ol016416e